(1R,2S,3R)-1-triethylsilyloxy-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enyl)-3-vinylcyclopentane | 932391-38-3

• 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: (1R,2S,3R)-1-triethylsilyloxy-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enyl)-3-vinylcyclopentane
• 英文别名: [(1R,2S,3R)-3-ethenyl-2-[(Z)-5-(oxan-2-yloxy)pent-2-enyl]cyclopentyl]oxy-triethylsilane
• CAS: 932391-38-3
• 化学式: C₂₃H₄₂O₃Si
• 分子量: 394.67
• InChiKey: ZQMLKWNSNYCWKE-IHESISLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R)-1-triethylsilyloxy-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enyl)-3-vinylcyclopentane 在 chromium(VI) oxide 、 盐酸 、 sodium chlorite 、 2-甲基-2-丁烯 、 pyridine-SO3 complex 、 bis(cyclohexanyl)borane 、 4-甲基苯磺酸吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 、 phosphate buffer 、 乙醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 12-羟基茉莉酸
  参考文献：
  名称：

  First total synthesis of tuberonic acid

  摘要：

  A vinyl group as an acetic acid side chain was attached to the optically active monoacetate of 4-cyclopentene-1,3-diol with CH2=CHMgBr, LiCl and a CuCN catalyst to produce the S(N)2-type product, from which the full carbon skeleton of tuberonic acid was constructed through Mitsunobu inversion, Claisen rearrangement, and Wittig reaction. At the last stage, the THP protective group was removed with MgBr2 in Et2O. The diastereomeric ratio of tuberonic acid and the trans isomer was 92:8 by H-1 NMR spectroscopy. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.035
• 作为产物：
  描述：

  (3aS,4R,6aR)-4-ethenyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 在 lithium aluminium tetrahydride 、 草酰氯 、 米帕明 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2S,3R)-1-triethylsilyloxy-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enyl)-3-vinylcyclopentane
  参考文献：
  名称：

  First total synthesis of tuberonic acid

  摘要：

  A vinyl group as an acetic acid side chain was attached to the optically active monoacetate of 4-cyclopentene-1,3-diol with CH2=CHMgBr, LiCl and a CuCN catalyst to produce the S(N)2-type product, from which the full carbon skeleton of tuberonic acid was constructed through Mitsunobu inversion, Claisen rearrangement, and Wittig reaction. At the last stage, the THP protective group was removed with MgBr2 in Et2O. The diastereomeric ratio of tuberonic acid and the trans isomer was 92:8 by H-1 NMR spectroscopy. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.035

文献信息

• Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA
  作者：Hisato Nonaka、Narihito Ogawa、Noriaki Maeda、Yong-Gang Wang、Yuichi Kobayashi

  DOI：10.1039/c0ob00218f

  日期：——

  epi-Jasmonic acid (epi-JA) and tuberonic acid (TA) were synthesized from the key aldehyde, all cis-2-(2-hydroxy-5-vinylcyclopentyl)acetaldehyde (14), which was in turn prepared stereoselectively from the (1R)-acetate of 4-cyclopentene-1,3-diol (10) through SN2-type allylic substitution with CH2CHMgBr followed by Mitsunobu inversion, Eschenmoser–Claisen rearrangement, and regioselective Swern oxidation

  表-茉莉酸 （Epi -JA） 和 胡椒酸 （TA）是由关键醛合成的，所有 顺-2-（2-羟基-5-乙烯基环戊基）乙醛（14），其又由（1R）-乙酸的乙酸酯立体选择性地制备。4-环戊烯-1,3-二醇（10）通过用CH 2 CHMgBr进行S N 2型烯丙基取代，然后进行Mitsunobu转化，埃申摩瑟–相应的bis-TES醚（13）的克莱森重排和区域选择性Swern氧化。醛14与[Ph 3 P（CH 2）Me] +的维蒂希反应溴−随后进行氧化Epi -JA（3）对反式异构体的立体选择性。相似地，TA（5）被合成。此外，上述发现已成功地用于提高以前合成的12-氧代PDA（1）。
• First total synthesis of tuberonic acid
  作者：Hisato Nonaka、Yong-Gang Wang、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2007.01.035

  日期：2007.3

  A vinyl group as an acetic acid side chain was attached to the optically active monoacetate of 4-cyclopentene-1,3-diol with CH2=CHMgBr, LiCl and a CuCN catalyst to produce the S(N)2-type product, from which the full carbon skeleton of tuberonic acid was constructed through Mitsunobu inversion, Claisen rearrangement, and Wittig reaction. At the last stage, the THP protective group was removed with MgBr2 in Et2O. The diastereomeric ratio of tuberonic acid and the trans isomer was 92:8 by H-1 NMR spectroscopy. (c) 2007 Elsevier Ltd. All rights reserved.