methyl (2S,3R)-2-vinyl-3-hydroxy-4-methylpentanoate | 1190930-32-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2S,3R)-2-vinyl-3-hydroxy-4-methylpentanoate
• CAS: 1190930-32-5
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: UKXVCBHSTSUGPK-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-2-vinyl-3-hydroxy-4-methylpentanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 methyl (2E,3R)-2-ethylidene-3-hydroxy-4-methylpentanoate 、 methyl (2Z,3R)-2-ethylidene-3-hydroxy-4-methylpentanoate
  参考文献：
  名称：

  The dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat: asymmetric synthesis of α-vinyl-β-hydroxycarboxylic acid derivatives and conversion to α-ethylidene-β-hydroxyesters (β-substituted Baylis–Hillman products)

  摘要：

  The synthesis of alpha-vinyl-beta-hydroxyesters and alpha-ethlylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) Via the dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat is described. High levels of syn-diastereoselectivity (up to >98% de) are observed for the dienolate aldol reaction with boron enolates, generated either directly with Bu2BOTf or by transmetalation of the potassium enolate with B-bromocatecholborane. Cleavage of the resultant syn-aldol products from the auxiliary gives alpha-vinyl-beta-hydroxyesters in >98% de and >98% ee. Subsequent isomerisation of the double bond into conjugation provides alpha-ethylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) in high diastereo- and enantiopurity (>= 91:9 |(E):(Z)| and >98% ee). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.004
• 作为产物：
  描述：

  甲醇 、 (4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxy-4'-methylpentanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one 在 正丁基锂 、 水 、 氯化铵 作用下， 以 甲醇 、 正戊烷 为溶剂， 以79%的产率得到methyl (2S,3R)-2-vinyl-3-hydroxy-4-methylpentanoate
  参考文献：
  名称：

  The dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat: asymmetric synthesis of α-vinyl-β-hydroxycarboxylic acid derivatives and conversion to α-ethylidene-β-hydroxyesters (β-substituted Baylis–Hillman products)

  摘要：

  The synthesis of alpha-vinyl-beta-hydroxyesters and alpha-ethlylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) Via the dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat is described. High levels of syn-diastereoselectivity (up to >98% de) are observed for the dienolate aldol reaction with boron enolates, generated either directly with Bu2BOTf or by transmetalation of the potassium enolate with B-bromocatecholborane. Cleavage of the resultant syn-aldol products from the auxiliary gives alpha-vinyl-beta-hydroxyesters in >98% de and >98% ee. Subsequent isomerisation of the double bond into conjugation provides alpha-ethylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) in high diastereo- and enantiopurity (>= 91:9 |(E):(Z)| and >98% ee). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.004

文献信息

• Synthesis of α-alkenyl-β-hydroxy adducts by α-addition of unprotected 4-bromocrotonic acid and amides with aldehydes and ketones by chromium(II)-mediated reactions
  作者：Ludger A. Wessjohann、Harry Wild、Leonildo A. Ferreira、Henri S. Schrekker

  DOI：10.1002/aoc.3488

  日期：2016.8

  The regioselective and diastereoselective chromium(II)‐mediated reactions of 4‐bromocrotonic acid or amides with aldehydes and ketones can proceed without the need to protect protic sites to generate the respective α‐alkenyl‐β‐hydroxy adducts, i.e. formally the addition of the α‐anion of a carboxylic acid or amide to an oxo‐compound is featured. Copyright © 2016 John Wiley & Sons, Ltd.

  可以进行4-溴巴豆酸或酰胺与醛和酮的区域选择性和非对映选择性铬（II）介导的反应，而无需保护质子位点以生成相应的α-烯基-β-羟基加合物，即正式添加具有羧酸或酰胺的α-阴离子与羰基化合物的特征。版权所有©2016 John Wiley＆Sons，Ltd.
• Cha, Joo Hwan; Pae, Ae Nim; Choi, Kyung Il Il, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 17, p. 2079 - 2081
  作者：Cha, Joo Hwan、Pae, Ae Nim、Choi, Kyung Il Il、Cho, Yong Seo、Koh, Hun Yeong、Lee, Eun

  DOI：——

  日期：——