(S)-3-Hydroxy-hex-5-enoic acid tert-butyl ester | 483316-37-6

• 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: (S)-3-Hydroxy-hex-5-enoic acid tert-butyl ester
• 英文别名: tert-Butyl (S)-3-hydroxyhex-5-enoate；tert-butyl (3S)-3-hydroxyhex-5-enoate
• CAS: 483316-37-6
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: KPVDTVYTDAZMOQ-QMMMGPOBSA-N

物化性质

• 沸点：
  261.7±28.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-Hydroxy-hex-5-enoic acid tert-butyl ester 在 咪唑 、 chromium dichloride 、 二甲基硫 、 Cr₂Cl₂ 、 戴斯-马丁氧化剂 、 臭氧 、 nickel dichloride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 (E)-(3S,9S)-3-(tert-Butyl-diphenyl-silanyloxy)-9-(2''-methoxymethoxymethyl-[2,4';2',4'']teroxazol-4-yl)-7-oxo-dec-5-enoic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric synthesis of a C1C19 fragment of ulapualide A

  摘要：

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01553-8
• 作为产物：
  描述：

  tert-butyl 3,4-epoxybutanoate 在 copper(l) iodide 、 (R,R)-Salen-Co 、 溶剂黄146 作用下， 生成 (S)-3-Hydroxy-hex-5-enoic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric synthesis of a C1C19 fragment of ulapualide A

  摘要：

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01553-8

文献信息

• Asymmetric synthesis of a C1C19 fragment of ulapualide A
  作者：Cassandra A. Celatka、James S. Panek

  DOI：10.1016/s0040-4039(02)01553-8

  日期：2002.9

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.