(1R,3R,6S,8S,9S,10R)-9,10-bis(benzenesulfonyl)-11-propan-2-ylidenetetracyclo[6.2.1.13,6.02,7]dodeca-2(7),4-diene | 119472-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3R,6S,8S,9S,10R)-9,10-bis(benzenesulfonyl)-11-propan-2-ylidenetetracyclo[6.2.1.13,6.02,7]dodeca-2(7),4-diene
• CAS: 119472-80-9
• 化学式: C₂₇H₂₆O₄S₂
• 分子量: 478.633
• InChiKey: DFRSYVOTSADHQH-GATLHOQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,6S,8S,9S,10R)-9,10-bis(benzenesulfonyl)-11-propan-2-ylidenetetracyclo[6.2.1.13,6.02,7]dodeca-2(7),4-diene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以62%的产率得到(1S,2R,5S,6R,7S,8S,9R,10R)-8,9-bis(benzenesulfonyl)-12-propan-2-ylidene-11-oxapentacyclo[4.4.1.12,5.17,10.01,6]tridec-3-ene
  参考文献：
  名称：

  Protocol for multiple functionalization of the [4]peristylane perimeter. Density relationships between the 2,4,6-trione, 2,4,6,8-tetrone, and related isopropylidene congeners

  摘要：

  DOI：

  10.1021/jo00275a017
• 作为产物：
  描述：

  4,7-二氢-4,7-甲桥-2H-茚 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、620.53 MPa 条件下， 反应 264.0h， 生成 (1R,3R,6S,8S,9S,10R)-9,10-bis(benzenesulfonyl)-11-propan-2-ylidenetetracyclo[6.2.1.13,6.02,7]dodeca-2(7),4-diene
  参考文献：
  名称：

  Protocol for multiple functionalization of the [4]peristylane perimeter. Density relationships between the 2,4,6-trione, 2,4,6,8-tetrone, and related isopropylidene congeners

  摘要：

  DOI：

  10.1021/jo00275a017

文献信息

• Consequences of Modulated Precompression along Reaction Coordinates. Synthesis, Crystallographic Structural Studies, and Rate of Intramolecular Dyotropy in an Extended Series of syn-Sesquinorbornene Disulfones
  作者：George A. O'Doherty、Robin D. Rogers、Leo A. Paquette

  DOI：10.1021/ja00103a004

  日期：1994.11

  In order to produce a broad range of syn-sesquinorbornene disulfones, (Z)-1,2-bis(phenylsulfonyI)ethylene was added in Diels-Alder fashion (high-pressure conditions) to tricyclo[5.2.1.0(2.6)]deca-2,5,8-trienes carrying isopropylidene or spirocyclopropane subunits at one or two sites. The central double bond in these adducts was then regiospecifically reduced with diimide, epoxidized with MCPBA, or cyclopropanated by [3 + 2] cycloaddition with diazomethane and subsequent photoinduced nitrogen extrusion. Each product in ah-three series was subjected to X-ray crystallographic analysis in order to quantify in the solid state the distance which each endo alpha-sulfonyl proton is required to traverse during dyotropic migration to the proximal norbornene double bond. The kinetics of these isomerizations were also determined, a relative reactivity scale was realized, and the values of k(ref) at 160 degrees C were found not to correlate well with the average distance across the intracavity gap. Although proximity of the reaction centers is clearly a prerequisite for smooth operation of the dyotropic shifts, modulation of this distance is not the sole contributor to reaction rate. Rather, the data are in agreement with the working hypothesis that various levels of steric compression within these disulfones facilitate passage over the relevant transition state to a greater or lesser degree depending on the magnitude of these nonbonded interactions.
• Extended functionalized of the fluted [4]peristylane perimeter
  作者：Leo A. Paquette、Chien-Chang Shen

  DOI：10.1016/s0040-4039(00)80419-0

  日期：1988.1
• PAQUETTE, LEO A.;SHEN, CHIEN-CHANG, TETRAHEDRON LETT., 29,(1988) N 33, C. 4069-4072
  作者：PAQUETTE, LEO A.、SHEN, CHIEN-CHANG

  DOI：——

  日期：——