(E)-1-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(Z)-5-(oxan-2-yloxy)pent-2-enyl]cyclopentyl]oct-1-en-3-one | 390746-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (E)-1-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(Z)-5-(oxan-2-yloxy)pent-2-enyl]cyclopentyl]oct-1-en-3-one
• CAS: 390746-24-4
• 化学式: C₃₅H₆₆O₅Si₂
• 分子量: 623.077
• InChiKey: SPLKFEBBAHUXTN-MKYDQPCWSA-N

物化性质

• 沸点：
  607.9±55.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.99
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(Z)-5-(oxan-2-yloxy)pent-2-enyl]cyclopentyl]oct-1-en-3-one 在 (S)-BINAL-H 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以96%的产率得到(E,3S)-1-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(Z)-5-(oxan-2-yloxy)pent-2-enyl]cyclopentyl]oct-1-en-3-ol
  参考文献：
  名称：

  iPF2α-III metabolism. First total synthesis of 2,3-dinor iPF2α-III, a primary β-oxidation metabolite

  摘要：

  The total synthesis of a primary iPF(2 alpha)-III metabolite, namely dinor iPF(2 alpha)-III 8, is described. The successful synthesis was finally accomplished by generating the carboxylic acid group at the end of the synthesis so as to avoid formation of an alpha,beta -unsaturated carboxylic acid, which is prone to undergo side reactions (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01794-4
• 作为产物：
  描述：

  methyl (E,4S,6R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[(4S)-2-sulfanylidene-1,3-dioxolan-4-yl]hex-2-enoate 在 偶氮二异丁腈 、 potassium tert-butylate 、 三正丁基氢锡 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 12.0h， 生成 (E)-1-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(Z)-5-(oxan-2-yloxy)pent-2-enyl]cyclopentyl]oct-1-en-3-one
  参考文献：
  名称：

  iPF2α-III metabolism. First total synthesis of 2,3-dinor iPF2α-III, a primary β-oxidation metabolite

  摘要：

  The total synthesis of a primary iPF(2 alpha)-III metabolite, namely dinor iPF(2 alpha)-III 8, is described. The successful synthesis was finally accomplished by generating the carboxylic acid group at the end of the synthesis so as to avoid formation of an alpha,beta -unsaturated carboxylic acid, which is prone to undergo side reactions (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01794-4

文献信息

• iPF2α-III metabolism. First total synthesis of 2,3-dinor iPF2α-III, a primary β-oxidation metabolite
  作者：Seongjin Kim、Young-Ju Jung、John A Lawson、Garret A FitzGerald、Joshua Rokach

  DOI：10.1016/s0040-4039(01)01794-4

  日期：2001.11

  The total synthesis of a primary iPF(2 alpha)-III metabolite, namely dinor iPF(2 alpha)-III 8, is described. The successful synthesis was finally accomplished by generating the carboxylic acid group at the end of the synthesis so as to avoid formation of an alpha,beta -unsaturated carboxylic acid, which is prone to undergo side reactions (C) 2001 Elsevier Science Ltd. All rights reserved.