methyl (2E,6E,10S)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate | 38005-88-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (2E,6E,10S)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate
• 英文别名: (S)-Juvenile hormone III；juvenile hormone III；(S)-(-)-JH III；10S-JH III；S-JH III；7-methyl-9-(3,3-dimethyloxivanyl)-3-methyl-2,6-nonadienoic acid methyl ester；methyl (2E,6E)-9-[(2S)-3,3-dimethyloxiran-2-yl]-3,7-dimethylnona-2,6-dienoate
• CAS: 38005-88-8
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: QVJMXSGZTCGLHZ-RATZTOCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E,6E,10S)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 6.3h， 以66%的产率得到(2E,6E)-(S)-10,11-epoxy-3,7,11-trimethyldodeca-2,6-dienoic acid
  参考文献：
  名称：

  First preparation of single-enantiomer juvenile hormone III acid and (R)-juvenile hormone III-d₃

  摘要：

  The (R)- and (S)-enantiomers of juvenile hormone (JH) III acid [(R)-2 and (S)-2] were prepared by the hydrolysis of (R)- and (S)-JH III [(R)-1 and (S)-1], respectively. Each enantiomer of 2 was purified by preparative reversed-phase high performance liquid chromatography in a single operation. (RS)-2 was methylated with CH3I and K2CO3 in MeCN, yielding (RS)-1. (R)-JH III-d3 [(R)-3], a single-enantiomer internal standard for quantification, was prepared from (R)-2 with CD3I and K2CO3 in MeCN.

  DOI：

  10.1080/14786411003752045
• 作为产物：
  描述：

  反式,反式-法尼基酸甲酯 在 吡啶 、 四氧化锇 、 甲基磺酰胺 、 potassium carbonate 、 甲基磺酰氯 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 28.5h， 生成 methyl (2E,6E,10S)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate
  参考文献：
  名称：

  Enantioselective Synthesis of Juvenile Hormone III in Three Steps from Methyl Farnesoate

  摘要：

  法诺斯酸甲酯的不对称二羟基化导致了 10、11 烯烃的区域选择性二羟基化，从而以高 ee 得到 (10S)and (10R) -(2E,6E)-10,11-dihydroxy-3,7,11-trimethyI-2,6-dodecadienoates (10S)和 (10R)。这些二元醇被转化为幼年激素 III 及其对映体。

  DOI：

  10.1055/s-1993-25939

文献信息

• Synthesis of both the enantiomers of juvenile hormone III
  作者：Kenji Mori、Hideto Mori

  DOI：10.1016/s0040-4020(01)83448-7

  日期：1987.1
• MORI, KENJI;MORI, HIDETO, TETRAHEDRON, 43,(1987) N 18, 4097-4106
  作者：MORI, KENJI、MORI, HIDETO

  DOI：——

  日期：——
• NARUSE, YUJI;ESAKI, TORU;YAMAMOTO, HISASHI, TETRAHEDRON, 44,(1988) N 15, C. 4747-4756
  作者：NARUSE, YUJI、ESAKI, TORU、YAMAMOTO, HISASHI

  DOI：——

  日期：——
• Enantioselective Synthesis of Juvenile Hormone III in Three Steps from Methyl Farnesoate
  作者：Gerard A. Crispino、K. Barry Sharpless

  DOI：10.1055/s-1993-25939

  日期：——

  The asymmetric dihydroxylation of methyl farnesoate resulted in regioselective dihydroxylation of the 10, 11 olefin to give the (10S)and (10R) -(2E,6E)-10,11-dihydroxy-3,7,11-trimethyI-2,6-dodecadienoates in high ee. These diols were converted to juvenile hormone III and its enantiomer.

  法诺斯酸甲酯的不对称二羟基化导致了 10、11 烯烃的区域选择性二羟基化，从而以高 ee 得到 (10S)and (10R) -(2E,6E)-10,11-dihydroxy-3,7,11-trimethyI-2,6-dodecadienoates (10S)和 (10R)。这些二元醇被转化为幼年激素 III 及其对映体。
• First preparation of single-enantiomer juvenile hormone III acid and (<i>R</i>)-juvenile hormone III-<i>d</i>₃
  作者：Akio Ichikawa、Makiko Takenaka、Hiroshi Ono

  DOI：10.1080/14786411003752045

  日期：2010.11.20

  The (R)- and (S)-enantiomers of juvenile hormone (JH) III acid [(R)-2 and (S)-2] were prepared by the hydrolysis of (R)- and (S)-JH III [(R)-1 and (S)-1], respectively. Each enantiomer of 2 was purified by preparative reversed-phase high performance liquid chromatography in a single operation. (RS)-2 was methylated with CH3I and K2CO3 in MeCN, yielding (RS)-1. (R)-JH III-d3 [(R)-3], a single-enantiomer internal standard for quantification, was prepared from (R)-2 with CD3I and K2CO3 in MeCN.