(2S)-1,2-dihydroxy-trans-4-octene | 100020-78-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-1,2-dihydroxy-trans-4-octene
• 英文别名: (4E)-oct-4-ene-1,2-diol；(2S,4E)-4-octene-1,2-diol；(E,2S)-oct-4-ene-1,2-diol
• CAS: 100020-78-8
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: FIGMGKCSXFYHCL-ZJELKQJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-1,2-dihydroxy-trans-4-octene 、 丙酮 在 对甲苯磺酸 作用下， 生成
  参考文献：
  名称：

  Synthesis of chiral 4-substituted 2-hydroxypent-4-enoic acid derivatives via diastereoselective ene reaction promoted by ZnBr2

  摘要：

  The diastereoselective carbonyl-ene reaction of various 1,1-disubstituted olefins with the chiral derivatives of glyoxylic acid, with Oppolzer's sultam 1a and 8-phenylmenthol 1b auxiliaries, was studied. The reaction proceeds effectively under undemanding conditions in the presence of equimolar or catalytic amount of ZnBr2 in good yield and at 72-94% de. Diastereoselectivities are usually slightly better with 8-phenylmenthyl glyoxylate 1b, however, the use of hemiacetal la is preferred because the products are often crystalline. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.007
• 作为产物：
  描述：

  (2'S)-(4E)-2'-hydroxy-oct-4'-enoic acid (1R,2S,5R)-8-phenylmenthyl ester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以52%的产率得到(2S)-1,2-dihydroxy-trans-4-octene
  参考文献：
  名称：

  Preparation of 8-phenylmenthol and its diastereomer, 2-epi,ent-8-phenylmenthol. A caveat

  摘要：

  DOI：

  10.1021/jo00354a032

文献信息

• Asymmetric induction in the ene reaction of glyoxylate esters of 8-phenylmenthol
  作者：James K. Whitesell、Apurba Bhattacharya、Charles M. Buchanan、H.H. Chen、Don Deyo、Dustin James、Chi-Ling Liu、Mark A. Minton

  DOI：10.1016/s0040-4020(01)90590-3

  日期：1986.1

  Bhattacharya, D.A. Aguilar and K. Henke, J. Chem. Soc. Chem. Commun. 989 (1982)) a highly efficient and effective method for the control of absolute stereochemistry through asymmetric induction in the ene reaction the chiral glyoxylate 1 with alkenes. We now have accumulated sufficient information on this process in terms of both its mechanistic details as well as its scope and applicability to a variety

  我们最近进行了交流（JK Whitesell，A。Bhattacharya，DA Aguilar和K. Henke，J。Chem。Soc。Chem。Commun。989（1982）），是一种通过非对称诱导控制绝对立体化学的高效方法。烯使手性乙醛酸酯1与烯烃反应。现在，我们就此过程的机理细节，范围和适用于各种情况的适用性等方面积累了足够的信息，以确保对这些反应进行更完整的介绍。
• WHITESELL J. K.; BHATTACHARYA A.; BUCHANAN C. M.; CHEN H. H.; DEYO D.; JA+, TETRAHEDRON, 42,(1986) N 11, 2993-3001
  作者：WHITESELL J. K.、 BHATTACHARYA A.、 BUCHANAN C. M.、 CHEN H. H.、 DEYO D.、 JA+

  DOI：——

  日期：——
• METHOD FOR THE SYNTHESIS OF AMINES AND AMINO ACIDS WITH ORGANOBORON DERIVATIVES
  申请人：UNIVERSITY OF SOUTHERN CALIFORNIA

  公开号：EP0923544B1

  公开（公告）日：2008-10-15
• Synthesis of chiral 4-substituted 2-hydroxypent-4-enoic acid derivatives via diastereoselective ene reaction promoted by ZnBr2
  作者：Piotr Kwiatkowski、Jacek Kwiatkowski、Jakub Majer、Janusz Jurczak

  DOI：10.1016/j.tetasy.2007.01.007

  日期：2007.2

  The diastereoselective carbonyl-ene reaction of various 1,1-disubstituted olefins with the chiral derivatives of glyoxylic acid, with Oppolzer's sultam 1a and 8-phenylmenthol 1b auxiliaries, was studied. The reaction proceeds effectively under undemanding conditions in the presence of equimolar or catalytic amount of ZnBr2 in good yield and at 72-94% de. Diastereoselectivities are usually slightly better with 8-phenylmenthyl glyoxylate 1b, however, the use of hemiacetal la is preferred because the products are often crystalline. (c) 2007 Elsevier Ltd. All rights reserved.
• Preparation of 8-phenylmenthol and its diastereomer, 2-epi,ent-8-phenylmenthol. A caveat
  作者：James K. Whitesell、Chi Ling Liu、Charles M. Buchannan、Hwang Hsing Chen、Mark A. Minton

  DOI：10.1021/jo00354a032

  日期：1986.2