((1E,3E)-2-Nona-1,3-dienyl)-[1,3]dithiane | 401901-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: ((1E,3E)-2-Nona-1,3-dienyl)-[1,3]dithiane
• 英文别名: 2-(1E,3E)-1,3-Nonadien-1-yl-1,3-dithiane；2-[(1E,3E)-nona-1,3-dienyl]-1,3-dithiane
• CAS: 401901-42-6
• 化学式: C₁₃H₂₂S₂
• 分子量: 242.45
• InChiKey: UTTQFKAPBVLEDW-LQPGMRSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((1E,3E)-2-Nona-1,3-dienyl)-[1,3]dithiane 在 potassium osmate(VI) 、 甲基磺酰胺 吡啶 、 2,6-二甲基吡啶 、 正丁基锂 、 18-冠醚-6 、 potassium tert-butylate 、 四丁基氟化铵 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 139.58h， 生成 8-[2-((E)-(3R,4S)-3,4-Dihydroxy-non-1-enyl)-[1,3]dithian-2-yl]-octanoic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids

  摘要：

  Pinellic acid from the tuber of Pinellia ternate, an active herbal component of the traditional Japanese herbal (Kampo) medicine Sho-seiryu-to, is a C18 trihydroxy fatty acid whose absolute stereochernistry has now been determined. All stereoisomers of pinellic acid were synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction in order to determine their absolute stereochemistries and adjuvant activities. Among this series of isomers, the (9S,12S,13S)-compound, which is a natural product, exhibited the most potent adjuvant activity. Spectral data for all of the stereoisomers of the 1,2-allylic diols were compared and related to their stereochemistries. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.06.088
• 作为产物：
  描述：

  1,3-丙二硫醇 、 反式-2,4-癸二烯醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到((1E,3E)-2-Nona-1,3-dienyl)-[1,3]dithiane
  参考文献：
  名称：

  松果酸的全合成，一种用于鼻流感疫苗的有效口服佐剂。确定相对和绝对构型

  摘要：

  从药用植物半夏中分离出的松香酸（1）具有有效的佐剂活性。通过该化合物的衍生化和CD激子手性法可以预期到松果酸的绝对构型。通过区域选择性的不对称二羟基化和立体选择性的还原，已经开发出一种聚合的合成壬二酸的途径。通过与天然和合成化合物的光谱数据进行比较，确定了半乳糖酸的绝对构型为9 S，12 S，13 S。

  DOI：

  10.1016/s0040-4039(01)02348-6

文献信息

• Total synthesis of pinellic acid, a potent oral adjuvant for nasal influenza vaccine. Determination of the relative and absolute configuration
  作者：Toshiaki Sunazuka、Tatsuya Shirahata、Kiminari Yoshida、Daisuke Yamamoto、Yoshihiro Harigaya、Takayuki Nagai、Hiroaki Kiyohara、Haruki Yamada、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1016/s0040-4039(01)02348-6

  日期：2002.2

  from a medicinal plant Pinelliae tuber, has potent adjuvant activity. The absolute configuration of pinellic acid was expected by derivatization of this compound and CD exciton chirality method. A convergent synthetic route to pinellic acid has been developed via regioselective asymmetric dihydroxylation and stereoselective reduction. The absolute configuration of pinellic acid was determined to be 9S

  从药用植物半夏中分离出的松香酸（1）具有有效的佐剂活性。通过该化合物的衍生化和CD激子手性法可以预期到松果酸的绝对构型。通过区域选择性的不对称二羟基化和立体选择性的还原，已经开发出一种聚合的合成壬二酸的途径。通过与天然和合成化合物的光谱数据进行比较，确定了半乳糖酸的绝对构型为9 S，12 S，13 S。
• US7560484B2
  申请人：——

  公开号：US7560484B2

  公开（公告）日：2009-07-14
• Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids
  作者：Tatsuya Shirahata、Toshiaki Sunazuka、Kiminari Yoshida、Daisuke Yamamoto、Yoshihiro Harigaya、Isao Kuwajima、Takayuki Nagai、Hiroaki Kiyohara、Haruki Yamada、Satoshi Ōmura

  DOI：10.1016/j.tet.2006.06.088

  日期：2006.10

  Pinellic acid from the tuber of Pinellia ternate, an active herbal component of the traditional Japanese herbal (Kampo) medicine Sho-seiryu-to, is a C18 trihydroxy fatty acid whose absolute stereochernistry has now been determined. All stereoisomers of pinellic acid were synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction in order to determine their absolute stereochemistries and adjuvant activities. Among this series of isomers, the (9S,12S,13S)-compound, which is a natural product, exhibited the most potent adjuvant activity. Spectral data for all of the stereoisomers of the 1,2-allylic diols were compared and related to their stereochemistries. (c) 2006 Published by Elsevier Ltd.