methyl (Z)-2-[(Z)-prop-1-enyl]tetradec-2-enoate | 354580-03-3

• 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: methyl (Z)-2-[(Z)-prop-1-enyl]tetradec-2-enoate
• CAS: 354580-03-3
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: VDFNTFKQENQKBB-CSULJURUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-[(Z)-prop-1-enyl]tetradec-2-enoate 在 Hydroquinone 1,4-phthalazinediyl diether 、 甲基磺酰胺 、 K₂OsO₃(OH)2 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以30%的产率得到litsenolide D₁
  参考文献：
  名称：

  Stereopure 1,3-butadiene-2-carboxylates and their conversion into non-racemic α-alkylidenebutyrolactone natural products by asymmetric dihydroxylation

  摘要：

  Dienoic esters 1 with the four possible permutations of the C=C configurations were prepared in two steps via non-stereoselective aldol additions followed by stereospecific beta -eliminations. Sharpless dihydroxylations of these esters yielded natural and unnatural alpha -alkylidene-beta -hydroxybutyrolactones 2. Among these were synthetic dihydromahubanolide B (cis,Z-2a), isodihydromahubanolide B (cis,E-2a) and, for the first time, litsenolide D-1 (ent-trans,Z-2b) and the enantiomer trans,E-2b of litsenolide D-2. Competitively, dihydroxyesters 10 were formed. (C) 2001 Elsevier Science Ltd. Al rights reserved.

  DOI：

  10.1016/s0040-4039(01)00598-6
• 作为产物：
  描述：

  反-2-戊酸甲酯 在 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 methyl (Z)-2-[(Z)-prop-1-enyl]tetradec-2-enoate
  参考文献：
  名称：

  Stereopure 1,3-butadiene-2-carboxylates and their conversion into non-racemic α-alkylidenebutyrolactone natural products by asymmetric dihydroxylation

  摘要：

  Dienoic esters 1 with the four possible permutations of the C=C configurations were prepared in two steps via non-stereoselective aldol additions followed by stereospecific beta -eliminations. Sharpless dihydroxylations of these esters yielded natural and unnatural alpha -alkylidene-beta -hydroxybutyrolactones 2. Among these were synthetic dihydromahubanolide B (cis,Z-2a), isodihydromahubanolide B (cis,E-2a) and, for the first time, litsenolide D-1 (ent-trans,Z-2b) and the enantiomer trans,E-2b of litsenolide D-2. Competitively, dihydroxyesters 10 were formed. (C) 2001 Elsevier Science Ltd. Al rights reserved.

  DOI：

  10.1016/s0040-4039(01)00598-6

文献信息

• Stereopure 1,3-butadiene-2-carboxylates and their conversion into non-racemic α-alkylidenebutyrolactone natural products by asymmetric dihydroxylation
  作者：Christian Harcken、Reinhard Brückner

  DOI：10.1016/s0040-4039(01)00598-6

  日期：2001.6

  Dienoic esters 1 with the four possible permutations of the C=C configurations were prepared in two steps via non-stereoselective aldol additions followed by stereospecific beta -eliminations. Sharpless dihydroxylations of these esters yielded natural and unnatural alpha -alkylidene-beta -hydroxybutyrolactones 2. Among these were synthetic dihydromahubanolide B (cis,Z-2a), isodihydromahubanolide B (cis,E-2a) and, for the first time, litsenolide D-1 (ent-trans,Z-2b) and the enantiomer trans,E-2b of litsenolide D-2. Competitively, dihydroxyesters 10 were formed. (C) 2001 Elsevier Science Ltd. Al rights reserved.