5-(trityloxy)pentanal | 258331-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-(trityloxy)pentanal
• 英文别名: 5-Trityloxypentanal
• CAS: 258331-72-5
• 化学式: C₂₄H₂₄O₂
• 分子量: 344.453
• InChiKey: XAYXDPVMLUFCQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(trityloxy)pentanal 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四溴化碳 、 三正丁基氢锡 、 臭氧 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 10.17h， 生成 6-oxohexyl benzoate
  参考文献：
  名称：

  Radical Cyclization Followed by the Fragmentation of Carbonyl Compounds: Effect of an α-Benzoyl Group

  摘要：

  To study a recently developed radical cyclization reaction followed by a fragmentation process in more detail, a series of a-benzoyl carbonyl compounds were prepared, including precursors with aldehyde and ketone moieties. Initiated by tributyltin hydride and AIBN, radical cyclizatiori followed by,fragmentation proceeded to give the desired. carbonyl-translocation products 4-benzoyl-5-pentanal, 4-benzoyl-5-pentanone, 5-benzoyl-6-hexanal, and 5-benzoyl-6-hexanone radical systems In comparison with,early-reports on radical cyclization reactions of alpha-oxy carbonyl compounds, neither a geminal dialkyl effect nor ,a conformationally rigid :system. was required to give the desired carbonyl translocation products This effect dearly proves that a benzoyl group serves as,a protecting group in these radical processes, which not only enhances cyclization efficiency but also increases the rate of the fragmentation step, eventually producing the desired carbonyl translocation products. These observations provide an alternative point of view in:the field of radical cyclization reactions. Since the fragmentation step could be enhanced by appropriately positioning an alpha-benzoyl group, these four radical processes could be used to convert the naturally occurring D-sugars, such as D-pentoses and D-hexoses, into rare deoxy-L-sugars. Furthermore, a cascade radical process involving radical cyclization and fragmentation followed by addition to the allyltin reagent was developed and is reported herein.

  DOI：

  10.1021/acs.joc.5b01754
• 作为产物：
  描述：

  1,5-戊二醇 在 4-二甲氨基吡啶 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 5-(trityloxy)pentanal
  参考文献：
  名称：

  带有天然叶绿素和细菌叶绿素潜在取代基的AD-二氢二吡喃的合成

  摘要：

  天然叶绿素和细菌叶绿素共享一个共同的反式取代吡咯啉环 D（17-丙酸，18-甲基），而多样性发生在环 A 中，尤其是在 3 位。已经合成了两种配备有类似天然 D 环取代基和可定制 A 环取代基的二氢二吡喃。该合成依赖于 Schreiber 修饰的 Nicholas 反应来构建立体化学定义的环 D 前体，即二烷基取代的 pent-4-ynoic 酸。完整丙酸的羧酸基团被证明是不可行的，因此检查了受保护的丙酸酯 (-CO 2 t Bu) 和几种潜在的丙醚。的叔-butyldiphenylsilyl保护丙醇取代基证明是令人满意的手性的反应N-酰化的恶唑烷酮，经过8个步骤以~30%的产率得到(2 S ,3 S )-2-(3-((叔丁基二苯基甲硅烷基)氧基)丙基)-3-甲基戊-4-炔酸。环 A 的两种变体，2-叔-butoxycarbonyl-3-Br/H-5-iodo-4-methylpyrrole，通过

  DOI：

  10.1021/acs.joc.1c01239

文献信息

• Yb(OTf)₃-Catalyzed Oxidation of Alcohols with Iodosylbenzene Mediated by TEMPO
  作者：Jean-Michel Vatèle

  DOI：10.1055/s-2006-948181

  日期：2006.8

  A rapid oxidation of primary and secondary alcohols ­using catalytic amounts of TEMPO and Yb(OTf)3 in combination with a stoichiometric amount of iodosylbenzene (PhIO) is described. This procedure operates at room temperature or above to afford carbonyl compounds in excellent yields without over-oxidation to carboxylic acids. Oxidation of primary alcohols in the ­presence of secondary alcohols proceeded with good selectivity.

  描述了一种使用催化量的TEMPO和Yb(OTf)3，以及计量量的碘苯 (PhIO) 对初级和二级醇进行快速氧化的方法。该方法在室温或更高温度下进行，可高效得到羰基化合物，而不会过氧化为羧酸。初级醇在存在二级醇的情况下进行氧化，选择性良好。
• Stereoselective Synthesis of Tri- and Tetrasubstituted α,β-Unsaturated Esters via Copper-catalyzed Coupling of Enol Triflates of β-Ketoesters with Grignard-based Zinc Ate Complexes
  作者：Mitsuaki Ide、Masaya Nakata

  DOI：10.1055/s-2001-17479

  日期：——

  Tri- and tetrasubstituted α,β-unsaturated esters were stereoselectively prepared via the copper-catalyzed couplings of the enol triflates of β-ketoesters with Grignard-based zinc ate complexes. Some insights into the mechanistic considerations are described.

  通过铜催化的β-酮酯的烯醇三氟甲磺酸酯与基于Grignard的锌配位复合物的偶联反应，立体选择性地合成了三取代和四取代的α,β-不饱和酯。文中还描述了一些对机理考虑的见解。
• Formal Alder-ene reaction of a bicyclo[1.1.0]butane in the synthesis of the tricyclic quaternary ammonium core of daphniglaucins
  作者：Masafumi Ueda、Maciej A.A. Walczak、Peter Wipf

  DOI：10.1016/j.tetlet.2008.07.179

  日期：2008.10

  A tricyclic substructure of the tetracyclic nitrogen core of the daphniglaucins was formed by an oxidative activation of the allyl side chain of a bicyclo[1.1.0]butylmethylamine, a spontaneous intramolecular formal Alder-ene reaction, and a selective cyclization of a triol intermediate.

  通过双环[1.1.0]丁基甲胺的烯丙基侧链的氧化活化、自发的分子内缩醛-烯反应和三醇中间体的选择性环化，形成了水蚤素四环氮核的三环亚结构。
• Synthetic studies on altohyrtins (spongistatins): synthesis of the C29–C44 (EF) portion
  作者：Takeshi Terauchi、Masataka Morita、Kyoko Kimijima、Yasuhiro Nakamura、Gouichirou Hayashi、Taisaku Tanaka、Naoki Kanoh、Masaya Nakata

  DOI：10.1016/s0040-4039(01)01069-3

  日期：2001.8

  C29–C44 portion of altohyrtins (spongistatins) has been prepared from 1,5-pentanediol and d-glucose in a stereoselective manner. The convergent synthesis relied on a coupling reaction of the C29–C37 vinyl bromide and the C38–C44 Weinreb amide, diastereoselective reduction of the C38 ketone, and stereoselective formation of the C33–C37 (E ring) acetal.

  Altohyrtins（海绵抑素）的C29-C44部分是由1,5-戊二醇和d-葡萄糖以立体选择性方式制备的。收敛合成依赖于C29–C37乙烯基溴与C38–C44韦氏酰胺的偶联反应，C38酮的非对映选择性还原以及C33–C37（E环）乙缩醛的立体选择性形成。
• On the Selective Deprotection of Trityl Ethers
  作者：Graham B. Jones、George Hynd、Justin M. Wright、Anu Sharma

  DOI：10.1021/jo9913255

  日期：2000.1.1