二(4-甲氧基苯基)(苯基)甲醇 | 40615-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 二(4-甲氧基苯基)(苯基)甲醇
• 英文名称: 4,4'-dimethoxytrityl alcohol
• 英文别名: bis(4-methoxyphenyl)(phenyl)methanol；bis(4-methoxyphenyl)-phenylmethanol
• CAS: 40615-35-8
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: XESTYUYENKNHHR-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  488.0±45.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2909499000
• 危险性防范说明：
  P264,P280,P337+P313,P305+P351+P338,P302+P352,P332+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  2-8°C

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4,4'-dimethoxytrityl methyl ether	125016-87-7	C22H22O3	334.415
  ——	4,4'-dimethoxytritylamine	136809-03-5	C21H21NO2	319.403
  4,4'-双甲氧基三苯甲基氯	4,4'-dimethoxytrityl chloride	40615-36-9	C21H19ClO2	338.834

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4,4'-Dihydroxy-triphenylmethylcarbinol	664-35-7	C19H16O3	292.334
  ——	4,4'-dimethoxytrityl methyl ether	125016-87-7	C22H22O3	334.415
  ——	diphenylmethyl p,p'-dimethoxytrityl ether	——	C34H30O3	486.61
  ——	1-[Butoxy-(4-methoxyphenyl)-phenylmethyl]-4-methoxybenzene	129247-62-7	C25H28O3	376.496
  4,4'-苄亚基二苯甲醚	4,4'-dimethoxytriphenylmethane	7500-76-7	C21H20O2	304.389
  ——	(+/-)-1-O-(4,4'-Dimethoxytrityl)propane-1,2-diol	129247-66-1	C24H26O4	378.468
  ——	1-[Cyclohexyloxy-(4-methoxyphenyl)-phenylmethyl]-4-methoxybenzene	1333311-79-7	C27H30O3	402.533
  ——	4,4'-dimethoxytrityl thiol	263746-51-6	C21H20O2S	336.455
  4,4'-双甲氧基三苯甲基氯	4,4'-dimethoxytrityl chloride	40615-36-9	C21H19ClO2	338.834
  ——	2,2-bis(4-methoxyphenyl)-2-phenylacetonitrile	120264-80-4	C22H19NO2	329.398

反应信息

• 作为反应物：
  描述：

  二(4-甲氧基苯基)(苯基)甲醇 在 tetrafluoroboric acid 、 lithium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.67h， 生成 保护-2'-脱氧尿苷
  参考文献：
  名称：

  使用无临时保护基团的 2'-脱氧尿苷向 2'-脱氧胞苷转化改进 5-羟甲基-2'-脱氧胞苷亚磷酰胺的合成

  摘要：

  5-羟甲基胞嘧啶最近被定性为人类 DNA 中的“第六个碱基”。为了能够对这种 DNA 修饰进行研究，我们报告了一种合成 5-羟甲基-2'-脱氧胞苷 ( 5-HOMe dC) 亚磷酰胺的改进方法，用于位点特异性掺入寡核苷酸中。为了最大限度地减少操作，我们采用了一种利用相转移催化的临时无保护基团 2'-脱氧尿苷到 2'-脱氧胞苷的转化过程。所需的5-HOMe dC 亚磷酰胺通过 6 个步骤从 2'-脱氧尿苷中获得，总产率为 24%。

  DOI：

  10.1016/j.bmcl.2010.12.098
• 作为产物：
  描述：

  S,S-diphenyl N2-isobutyryl-5'-O-dimethoxytritylguanosine 3'-phosphorodithioate 在 三氟乙酸 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 1.13h， 生成 二(4-甲氧基苯基)(苯基)甲醇
  参考文献：
  名称：

  1,2-二异丁酰氧基乙烯基对鸟嘌呤残基的新型保护方式

  摘要：

  在低聚脱氧鸟苷酸酯的合成中，一种新的保护基1，2-二异丁酰氧基乙烯基已成功地用于鸟嘌呤残基的保护。

  DOI：

  10.1016/s0040-4039(00)85820-7

文献信息

• Copper(II)nitrate catalyzed regioselective protection of primary alcohols with 4,4′-dimethoxytrityl and 2,7-dimethyl-9-phenyl xanthen-9-yl groups in nucleosides and carbohydrates
  作者：Srishylam Penjarla、S. Rajendra Prasad、Dhande Sudhakar Reddy、Shyamapada Banerjee、Santhosh Penta、Yogesh S. Sanghvi

  DOI：10.1080/15257770.2018.1460480

  日期：2018.4.3

  ABSTRACT Regioselective protection of primary hydroxyl group in nucleoside and carbohydrate analogs was accomplished using dimethoxytrityl alcohol (DMTr-OH) or dimethylpixyl alcohol (DMPx-OH) in presence of copper(II)nitrate as a Lewis acid catalyst. Excellent selectivity was observed for the protection of primary hydroxyl group over secondary while glycosidic bond remain unaffected. Utility of this

  摘要 在作为路易斯酸催化剂的硝酸铜 (II) 存在下，使用二甲氧基三苯甲醇 (DMTr-OH) 或二甲基苯甲醇 (DMPx-OH) 实现了核苷和碳水化合物类似物中伯羟基的区域选择性保护。观察到优异的选择性保护伯羟基而不是仲羟基，而糖苷键不受影响。通过脂肪族无环和环状二醇的 DMTr 和 DMPx 保护进一步举例说明了该方法的实用性。
• MELANIN PRODUCTION INHIBITOR
  申请人：Yokoyama Kouji

  公开号：US20110243865A1

  公开（公告）日：2011-10-06

  Disclosed is a melanin production inhibitor which has an excellent inhibitory activity on the production of melanin and is highly safe. The melanin production inhibitor comprises a compound represented by general formula (1) (excluding clotrimazole), and/or a pharmacologically acceptable salt thereof. In the formula, A1, A2 and A3 are independently selected from a hydrogen atom, an aryl group which may have a substituent, and an aromatic heterocyclic group which may have a substituent, wherein at least one of A1, A2 and A3 is selected from the aryl group and the aromatic heterocyclic group, the total number of carbon atoms contained in A1, A2 and A3 is 6 to 50 and, when at least two of A1, A2 and A3 represent the aryl groups or the aromatic heterocyclic groups, the adjacent two aryl or aromatic heterocyclic groups may be bound to each other via an alkyl chain or an alkenyl chain to form a ring; m represents an integer of 0 to 2; X represents a hetero atom, a hydrogen atom, or a carbon atom; R1 and R2 are independently selected from a hydrogen atom and an oxo group, wherein when one of R1 and R2 is an oxo group, the other is not present; and R3 is selected from a hydrogen atom, and a C 1-8 hydrocarbon group in which one or some of hydrogen atoms or carbon atoms may be substituted by a hetero atom or hetero atoms, wherein the number of R3's present in the compound corresponds to the number of X's and, when two or more R3's are present, the R3's are independently present and the adjacent two R3's may be bound to each other to form, together with X, a ring, and the terminal of R3 may be bound to a carbon atom to which A1, A2 and A3 are bound, thereby forming a ring.

  披露了一种黑色素生产抑制剂，它对黑色素的生产具有出色的抑制活性且高度安全。该黑色素生产抑制剂包括由通用公式（1）表示的化合物（不包括克霉唑）和/或其药理上可接受的盐。在公式中，A1、A2和A3独立地选自氢原子、可能带有取代基的芳基团和可能带有取代基的芳香杂环团，其中至少A1、A2和A3之一选自芳基团和芳香杂环团，A1、A2和A3中包含的碳原子总数为6至50，并且当至少两个A1、A2和A3表示芳基团或芳香杂环团时，相邻的两个芳基或芳香杂环团可以通过烷基链或烯基链相互连接形成环；m代表0至2的整数；X代表异原子、氢原子或碳原子；R1和R2独立地选自氢原子和氧代基，其中当R1和R2之一是氧代基时，另一个不出现；R3选自氢原子和C 1-8 碳氢化合物组，其中一些或所有的氢原子或碳原子可能被异原子或异原子取代，其中化合物中存在的R3的数量对应于X的数量，并且当存在两个或更多R3时，R3独立地存在，并且相邻的两个R3可以相互连接以与X一起形成环，并且R3的末端可以与A1、A2和A3连接的碳原子结合，从而形成环。
• 1,1,1,3,3,3-Hexafluoro-2-propanol for the removal of the 4,4′-DimethoxytrityI protecting group from the 5′-hydroxyl of acid-sensitive nucleosides and nucleotides
  作者：Nelson J. Leonard、Neelima

  DOI：10.1016/0040-4039(95)01673-6

  日期：1995.10

  1,1,1,3,3,3-Hexafluoro-2-propanol is introduced as a suitable reagent and solvent for the detritylution of 5′-O-(4,4′-dimethoxytrityl)-nucleosides and -deoxynucleosides, especially those that are susceptible to N-glycosyl cleavage under more strongly acidic conditions.

  引入1,1,1,3,3,3-六氟-2-丙醇作为合适的试剂和溶剂，用于5'- O-（4,4'-二甲氧基三苯甲基）-核苷和-deoxynucleosides，特别是那些的脱三苯胺稀释在更强的酸性条件下易受N-糖基裂解的影响。
• N-Tritylhydroxylamines: preparations, structures, base strengths, and reactions with nitrous acid and perchloric acid
  作者：Moisés Canle L.、William Clegg、Ibrahim Demirtas、Mark R. J. Elsegood、Johanna Haider、Howard Maskill、Peter C. Miatt

  DOI：10.1039/b103569j

  日期：——

  N-Trityl, N-(4-methoxytrityl), N-(4,4′-dimethoxytrityl), and N-(4,4′,4″-trimethoxytrityl) derivatives of hydroxylamine, O-methylhydroxylamine, and O-benzylhydroxylamine have been prepared and characterised. Additionally, N,O-ditrityl- and N,O-bis(4,4′-dimethoxytrityl)-hydroxylamines have been made, and the X-ray crystal structure of the former has been determined. The pKa value of O-benzylhydroxylammonium in water (6.2) and of its N-trityl analogue in aqueous acetonitrile (7.5) have been measured. The N-tritylhydroxylamines all decompose under aqueous acidic conditions to give the corresponding trityl alcohols, and rate constants for uncatalysed and hydronium ion catalysed reactions of N-(4,4′-dimethoxytrityl)-O-methylhydroxylamine have been measured by stopped flow kinetics at 25 °C. This compound compares in reactivity with N-alkyl-N-(4,4′-dimethoxytrityl)amines rather than with 4,4′-dimethoxytritylamine. Attempted nitrosation of N-tritylhydroxylamine and its O-alkyl derivatives gave trityl alcohol, the intermediate N-nitroso compound being detectable but too unstable to isolate. From N-trityl-O-benzylhydroxylamine, attempted nitrosation led to the formation of triphenylmethane in addition to trityl alcohol, benzyl alcohol, and trityl benzyl ether. The mildly acidic conditions used for attempted nitrosation of methoxy-substituted N-tritylhydroxylamines led to deamination before addition of the nitrosating agent.

  已经制备并表征了羟胺、O-甲基羟胺和O-苄基羟胺的N-三苯甲基、N-(4-甲氧基三苯甲基)、N-(4,4'-二甲氧基三苯甲基)和N-(4,4',4''-三甲氧基三苯甲基)衍生物。此外，还制备了N,O-二三苯甲基和N,O-双(4,4'-二甲氧基三苯甲基)羟胺，并测定了前者的X射线晶体结构。测量了O-苄基羟胺盐在水中(pKa 6.2)及其N-三苯甲基类似物在乙腈水溶液中(pKa 7.5)的pKa值。所有N-三苯甲基羟胺在酸性水溶液条件下均分解生成相应的三苯甲基醇，通过停流动力学在25°C下测量了N-(4,4'-二甲氧基三苯甲基)-O-甲基羟胺的无催化反应和质子催化反应的速率常数。该化合物的反应性介于N-烷基-N-(4,4'-二甲氧基三苯甲基)胺和4,4'-二甲氧基三苯甲基胺之间。试图对N-三苯甲基羟胺及其O-烷基衍生物进行亚硝化反应，生成三苯甲基醇，中间体N-亚硝基化合物可检测到但过于不稳定而无法分离。从N-三苯甲基-O-苄基羟胺出发，试图进行亚硝化反应除了生成三苯甲基醇外，还形成了三苯甲烷、苄醇和三苯甲基苄基醚。对甲氧基取代的N-三苯甲基羟胺试图进行亚硝化反应时的轻微酸性条件，在加入亚硝化试剂之前先发生了脱氨反应。
• Cationic hydrogenation of benzyl alcohols and arylethylenes using acridane derivatives as hindered NADH models
  作者：Serjinder Singh、Sarbjeet Chhina、Vijay K. Sharma、Satbir S. Sachev

  DOI：10.1039/c39820000453

  日期：——

  Secondary and tertiary benzyl alcohols and arylethylenes are efficiently reduced by acridane derivatives (1) in the presence of trifluoroacetic acid in dichloromethane.

  在二氯甲烷中三氟乙酸存在下，a啶衍生物（1）可有效还原仲和叔苄醇和芳基乙烯。