(R)-异丙基环氧乙烷 | 82378-47-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: (R)-异丙基环氧乙烷
• 英文名称: (R)-2-isopropyloxirane
• 英文别名: (R)-isopropyloxirane；(R)-1,2-epoxy-3-methylbutane；(2R)-2-isopropyloxirane；(2R)-2-(propan-2-yl)oxirane；(2R)-2-propan-2-yloxirane
• CAS: 82378-47-0
• 化学式: C₅H₁₀O
• 分子量: 86.1338
• InChiKey: REYZXWIIUPKFTI-YFKPBYRVSA-N

物化性质

• 沸点：
  75 ºC
• 密度：
  0.893
• 闪点：
  -8 ºC

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-异丙基环氧乙烷 在 甲基锂 、 copper(l) cyanide 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以81%的产率得到(S)-2-methyl-3-pentanol
  参考文献：
  名称：

  (S)-2-Methylpent-3-yl 3,13-Dimethylpentadecanoate 的四种立体异构体的合成，一种袋虫 MothClania variegate 的性信息素，使用二级磺酸盐的立体定向反转作为关键步骤

  摘要：

  某些鳞翅目物种的雌性会产生具有甲基支链结构的新型性信息素，例如由袋螟蛾 Clania variegate 分泌的 2-methylpent-3-yl 3,13-methylpentadecanoate。最近，我们建立了一种简单的制备方法，通过利用衍生自 (S)- 和 (R)-环氧丙烷的手性仲甲苯磺酸酯的 SN2 反应合成甲基支链结构单元。这些构建块的有用性通过它们在袋虫信息素中酸部分的所有四种立体异构体的合成中的应用得到了证明。通过对映选择性 HPLC 分析确认所有结构单元的对映体纯度。我们发现二级甲磺酸盐优于相应的甲苯磺酸盐，因为它避免了消除副反应，即使在高温（150°C）下也未观察到 SN2 反应中的外消旋化。最后，每种旋光酸都用（S）-2-甲基-3-戊醇酯化，这是通过从（S）-缬氨酸开始的新路线合成的。

  DOI：

  10.1002/ejoc.201300874
• 作为产物：
  描述：

  D-缬氨酸 在 盐酸 、 dimethyl sulfide borane 、 potassium hydroxide 、 sodium nitrite 作用下， 以 乙醚 、 正己烷 、 水 为溶剂， 反应 1.0h， 生成 (R)-异丙基环氧乙烷
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor

  摘要：

  The beta(2)-adrenergic receptor (beta(2)-AR) agonist [H-3]-(R,R')-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (K-i values) of the stereoisomers of a series of 4'-methoxyfenoterol analogs in which the length of the alkyl substituent at alpha' position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [H-3]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the beta(2)-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the alpha' position. The results also indicate that the K-i values obtained using [H-3]-(R,R')methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [H-3]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the beta(2)-AR conformation probed by [H-3]-(R,R')-4'-methoxyfenoterol. The CoMFA model of the agonist-stabilized beta(2)-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the beta(2)-AR is governed to a greater extend by steric effects than binding to the [H-3]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.030

文献信息

• Isolation, Structure, and Total Synthesis of the Marine Macrolide Mangrolide D
  作者：Junyu Gong、Wei Li、Peng Fu、John MacMillan、Jef K. De Brabander

  DOI：10.1021/acs.orglett.9b01126

  日期：2019.4.19

  The isolation, characterization, and total synthesis of the macrocyclic polyene mangrolide D is reported. A 16-step total synthesis relies on robust Suzuki and ring-closing metathesis reactions, and an iron-catalyzed hydroazidation of an exomethylene substituted tetrahydropyran as a key step for the synthesis of the appended 4- epi-vancosamine sugar. Although mangrolide D did not display antibiotic

  报道了大环多烯芒果苷D的分离，表征和全合成。16个步骤的总合成依赖于强大的Suzuki和闭环复分解反应，并且铁催化的exomethyl取代的四氢吡喃的加氢叠氮反应是合成附加的4- Epi-vancosamine糖的关键步骤。尽管Mangrolide D没有显示抗生素活性，但这项工作应证明能够合成具有几乎相同的大环骨架的抗结核性天花霉素。
• Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A
  作者：Hiromu Hattori、Joel Roesslein、Patrick Caspers、Katja Zerbe、Hideki Miyatake-Ondozabal、Daniel Ritz、Georg Rueedi、Karl Gademann

  DOI：10.1002/anie.201805770

  日期：2018.8.20

  The macrocyclic antibiotic mangrolide A has been described to exhibit potent activity against a number of clinically important Gram‐negative pathogens. Reported is the first enantioselective total synthesis of mangrolide A and derivatives. Salient features of this synthesis include a highly convergent macrocycle preparation, stereoselective synthesis of the disaccharide moiety, and two β‐selective

  大环抗生素甜菊内酯A被描述为对许多临床上重要的革兰氏阴性病原体表现出有效的活性。报道了第一个对映选择性全合成芒果内酯A及其衍生物。该合成的显着特征包括高度收敛的大环化合物制备，二糖部分的立体选择性合成以及两个β选择性糖基化。芒果内酯A及其类似物的合成能够重新检查其对细菌病原体的活性，并且仅观察到最小的活性。
• Synthesis of Chiral Amino Alcohols Embodying the Bispidine Framework and Their Application as Ligands in Enantioselectively Catalyzed Additions to CO and CC Groups
  作者：Jan Spieler、Oliver Huttenloch、Herbert Waldmann

  DOI：10.1002/(sici)1099-0690(200002)2000:3<391::aid-ejoc391>3.0.co;2-r

  日期：2000.2

  course of enantioselective transformations, bispidine amino alcohols built up by these two routes were investigated as chiral ligands in the enantioselectively catalyzed addition of diethylzinc to aldehydes and chalcone. In general, tridentate ligands containing one chiral amino alcohol fragment and a second amino substituent without a stereogenic center were more efficient than tetradentate ligands with

  已经开发了两种普遍适用的合成包含双吡啶骨架的手性氨基醇的路线。在线性路线 A 中，双吡啶骨架是由手性伯胺通过中间体形成哌啶酮和双吡啶酮依次构建的。在收敛路线 B ​​中，首先形成非手性双吡啶，然后通过氮碱与手性亲电试剂的反应引入 N-取代基。为了确定双吡啶核心及其 N 取代基是否能影响对映选择性转化的空间过程，研究了通过这两种途径构建的双吡啶氨基醇作为手性配体在二乙基锌对醛和查耳酮的对映选择性催化加成中。一般来说，含有一个手性氨基醇片段和没有立体中心的第二个氨基取代基的三齿配体比具有两个氨基醇结构单元的四齿配体更有效。使用最好的配体，二乙基锌对芳香族和脂肪族醛的对映选择性加成以 83-98% ee 进行，二乙基锌向查耳酮的镍催化加成达到 85% ee。
• Synthetic Studies of Vitamin D Analogues. XVII.Synthesis and Differentiation-Inducing Activity of 1α, 24-Dihydroxy-22-oxavitamin D&lt;SUB&gt;3&lt;/SUB&gt; Analogues and Their 20(R)-Epimers
  作者：Noboru KUBODERA、Hiroyoshi WATANABE、Katsuhito MIYAMOTO、Masahiko MATSUMOTO、Setsu MATSUOKA、Takehiko KAWANISHI

  DOI：10.1248/cpb.41.1659

  日期：——

  Four vitamin D3 analogues, 1α, 24(S)-and 1α, 24(R)-dihydroxy-22-oxavitamin D3 (5 and 6) and their 20(R)-epimers (7 and 8) were synthesized from the 20(S)-alcohol (10). In tests of activity to induce differentiation of human myeloid leukemia cells (HL-60) to macrophages, 5 showed comparable activity to 1α, 25-dihydroxy-22-oxavitamin D3 (OCT) (2), and the other three analogues (6, 7 and 8) were less active than OCT (2). The binding properties of these analogues to the chick embryonic intestinal 1α, 25-dihydroxyvitamin D3 (1) receptor were evaluated. Furthermore, 20(R)-OCT (9) was synthesized and its biological properties were compared with those of OCT (2) and the 20(R)-epimers (7 and 8).

  合成了四种维生素D3类似物，1α、24(S)-和1α、24(R)-二羟基-22-氧维生素D3（5和6）及其20(R)-表异构体（7和8），它们均来源于20(S)-醇（10）。在诱导人类骨髓白血病细胞（HL-60）向巨噬细胞分化的活性测试中，5表现出与1α、25-二羟基-22-氧维生素D3（OCT）（2）相当的活性，而其他三个类似物（6、7和8）的活性均低于OCT（2）。评估了这些类似物与小鸡胚胎肠道1α、25-二羟基维生素D3（1）受体的结合特性。此外，合成了20(R)-OCT（9），并将其生物特性与OCT（2）和20(R)-表异构体（7和8）的特性进行了比较。
• 5- substituted tetralones as inhibitors of ras farnesyl trransferase
  申请人：——

  公开号：US20040044057A1

  公开（公告）日：2004-03-04

  The present invention provides novel 5-substituted tetralones of Formulas (I), (II), (III) and (IV) and pharmaceutically acceptable salts, esters, amides, and prodrugs thereof, which are useful for treating and preventing uncontrolled or abnormal proliferation of tissues, such as cancer, atherosclerosis, restenosis, and psoriasis. Specifically, the present invention relates to compounds that inhibit the farnesyl transferase enzyme. 1

  本发明提供了式(I)、(II)、(III)和(IV)的新型5-取代四酮及其药学上可接受的盐、酯、酰胺和前药，用于治疗和预防组织的不受控制或异常增殖，如癌症、动脉粥样硬化、再狭窄和银屑病。具体而言，本发明涉及抑制法尼基转移酶酶的化合物。