2-methylene-4-phenylpent-4-en-1-ol | 1015098-94-8

• 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: 2-methylene-4-phenylpent-4-en-1-ol
• CAS: 1015098-94-8
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: VFIADZDMQLIKDI-UHFFFAOYSA-N

物化性质

• 沸点：
  302.6±21.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-methylene-4-phenylpent-4-en-1-ol 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 偶氮二甲酸二异丙酯 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 对二甲苯 、 mineral oil 为溶剂， 生成 8a-methyl-8-methylene-6-phenyl-2-tosyloctahydro-1H-3a,6-methanocyclohepta[c]pyrrole
  参考文献：
  名称：

  分子内铑催化的二亚乙烯基环丙烷的[(3+2+2)]碳环化反应：倍半萜烯(+)-Zizaene的简洁立体选择性全合成

  摘要：

  描述了与 1,4- 和 1,5- 跳过二烯连接的亚烷基环丙烷 (ACP) 的分子内铑催化 [(3+2+2)] 碳环化反应的发展。这种转变为构建具有多达三个四级中心的桥联三环化合物提供了一种新方法，适用于合成具有挑战性的生物活性天然产物。例如，通过从市售起始材料分十步进行倍半萜烯 (+)-zizaene 的简明不对称全合成，说明了这种转化的合成效用。

  DOI：

  10.1021/jacs.2c10923

文献信息

• Enantioselective Syntheses of Various Chiral Multicyclic Compounds with Quaternary Carbon Stereocenters by Catalytic Intramolecular Cycloaddition
  作者：Takanori Shibata、Yu-ki Tahara、Kohei Tamura、Kohei Endo

  DOI：10.1021/ja0762083

  日期：2008.3.1

  The intramolecular cycloaddition of 1,n-diene-ynes (n = 4-6), where alkyne and alkene moieties are connected by a 1,1-disubstituted alkene, was examined using a chiral rhodium catalyst, and various types of cycloadducts with quaternary carbon stereocenter(s) were obtained in high to excellent enantiomeric excess. In the case of 1,4-diene-ynes, tricyclic, bicyclic, and spirocyclic compounds were obtained depending upon the substituents at the 2-position of the 1,4-diene moiety and those at their alkyne termini. On the other hand, 1,5- and 1,6-diene-ynes gave tricyclic and bicyclic compounds, which included medium-sized ring systems. The mechanistic considerations for different reaction pathways and the synthetic transformation of tricyclic products into functionalized spirocyclic compounds are also described. The reaction of enediynes, where two alkyne moieties are connected by a 1,1-disubstituted alkene, was also examined, and sterically strained tricyclic compounds with two carbon stereocenters were obtained.
• Intramolecular Rhodium-Catalyzed [(3+2+2)] Carbocyclization Reactions with Dienylidenecyclopropanes: A Concise and Stereoselective Total Synthesis of the Sesquiterpene (+)-Zizaene
  作者：Yu Zhu、Jie Zheng、P. Andrew Evans

  DOI：10.1021/jacs.2c10923

  日期：——

  for the construction of bridged tricyclic compounds with up to three quaternary centers, which are suitable for the synthesis of challenging bioactive natural products. For instance, the synthetic utility of this transformation is illustrated through a concise asymmetric total synthesis of the sesquiterpene (+)-zizaene in ten steps from a commercially available starting material.

  描述了与 1,4- 和 1,5- 跳过二烯连接的亚烷基环丙烷 (ACP) 的分子内铑催化 [(3+2+2)] 碳环化反应的发展。这种转变为构建具有多达三个四级中心的桥联三环化合物提供了一种新方法，适用于合成具有挑战性的生物活性天然产物。例如，通过从市售起始材料分十步进行倍半萜烯 (+)-zizaene 的简明不对称全合成，说明了这种转化的合成效用。