exo-3-thiabicyclo<3.2.0>heptane-6,7-dicarboxylic anhydride 3,3-dioxide | 82535-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: exo-3-thiabicyclo<3.2.0>heptane-6,7-dicarboxylic anhydride 3,3-dioxide
• 英文别名: 3,3-dioxo-3-thiabicyclo<3.2.0>heptane-6,7-dicarboxylic anhydride；exo-3-thiabicyclo[3.2.0]heptane-6,7-dicarboxylic anhydride 3,3-dioxide；(1S,2R,6S,7R)-9,9-dioxo-4-oxa-9λ6-thiatricyclo[5.3.0.02,6]decane-3,5-dione
• CAS: 82535-14-6
• 化学式: C₈H₈O₅S
• 分子量: 216.215
• InChiKey: XDMVLZSXVDCDKD-GUCUJZIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.02
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  exo-3-thiabicyclo<3.2.0>heptane-6,7-dicarboxylic anhydride 3,3-dioxide 生成 cis-hexa-1,5-diene-3,4-dicarboxylic acid anhydride
  参考文献：
  名称：

  E，Z -1,5-二烯的简单，立体控制的合成

  摘要：

  3-噻二环[3.2.0]庚烷-6,7-二羧酸酐的3,3-二氧化物（1）可以作为E，Z -1,5-二烯的一般合成前体，例如（4a – e）通过功能化，然后热挤出SO 2。

  DOI：

  10.1039/c39820000325
• 作为产物：
  描述：

  马来酸酐 、 3-环丁烯砜 以 丙酮 为溶剂， 生成 exo-3-thiabicyclo<3.2.0>heptane-6,7-dicarboxylic anhydride 3,3-dioxide
  参考文献：
  名称：

  Conformation and hydrogen bonding for the bicyclic compound 3-thiabicyclo[3.2.0]heptane-6,7-dicarboxylic acid 3,3-dioxide

  摘要：

  The initial goal of this work was to verify the geometry of the product of a photochemical reaction, viz. the title compound, C8H10O6S, (II). Our crystallographic study firmly establishes the cis-anti-cis nature of the substituents on the cyclobutane ring. The geometry is also designated as exo, where exo signifies that the five-membered ring is on the opposite side of the central cyclobutane ring from the carboxylic acid substituents. The structure determination reveals two molecules, A and B, in the asymmetric unit that display substantially different conformations of the bicyclic core: the cyclobutane ring puckering angles are 22 and 3 degrees, and the sulfolane ring conformations are twist (S-exo) and envelope (S-endo). Intrigued by this variation, we then compared the conformations of other molecules in the Cambridge Structural Database that have sulfolane rings fused to cyclobutane rings. In this class of compound, there are five examples of saturated cyclobutane rings, with ring puckering angles ranging from 3 to 35 degrees. The sulfolane rings were more similar: four of the six molecules exhibit envelope conformations with S-endo, as in molecule B of ( II). Despite the conformational differences, the hydrogen-bonding scheme for both molecules is similar: carboxyl -OH groups form hydrogen bonds with carboxyl and sulfone O atoms. Alternating A and B molecules joined by hydrogen bonds between sulfone O atoms and carboxyl -OH groups form parallel chains that extend in the ac plane. Other hydrogen bonds between the carboxyl groups link the chains along the b axis.

  DOI：

  10.1107/s0108270108022439

文献信息

• Photocycloaddition of 2,5-dihydrothiophen SS-dioxides to α,β-unsaturated cyclic anhydrides. Synthesis of 10-hydroxygeraniol
  作者：John R. Williams、Charles Lin

  DOI：10.1039/c39810000752

  日期：——

  10-Hydroxygeraniol (6c) was synthesized from 2,5-dihydro-3-methythiophen SS-dioxide (1b) and citraconic anhydrid (2b) in 48% overall yield via irradiation followed by thermal extrusion of SO2 from the intermediate photoadduct (3b) and a Cope rearrangement of the resulting divinyl diester (5b).

  由2,5-二氢-3-甲基噻吩SS-二氧化物（1b）和柠康酸酐（2b）通过辐照，然后从中间光加合物（3b）热挤出SO 2合成10-羟基香叶醇（6c））和相应的二乙烯基二酯的应对重排（5b）。
• A simple, stereocontrolled synthesis of E,Z-1,5-dienes
  作者：J. I. G. Cadogan、Caroline M. Buchan、Ian Gosney、Brendan J. Hamill、Leo M. McLaughlin

  DOI：10.1039/c39820000325

  日期：——

  The readily available 3,3-dioxide (1) of 3-thiabicyclo[3.2.0]heptane-6,7-dicarboxylic anhydride acts as a general synthetic precursor for E,Z-1,5-dienes such as (4a–e)via functionalisation followed by thermal extrusion of SO2.

  3-噻二环[3.2.0]庚烷-6,7-二羧酸酐的3,3-二氧化物（1）可以作为E，Z -1,5-二烯的一般合成前体，例如（4a – e）通过功能化，然后热挤出SO 2。
• Synthesis of 1,5-dienes via [2 + 2] photocycloadditions between 2,5-dihydrothiophene 1,1-dioxides (sulfolenes) and .alpha.,.beta.-unsaturated cyclic ketones and anhydrides. Synthesis of 10-hydroxygeraniol
  作者：John R. Williams、Charles Lin、Daniel F. Chodosh

  DOI：10.1021/jo00350a074

  日期：1985.12
• Conformation and hydrogen bonding for the bicyclic compound 3-thiabicyclo[3.2.0]heptane-6,7-dicarboxylic acid 3,3-dioxide
  作者：Virginia B. Pett、LeRoy W. Haynes

  DOI：10.1107/s0108270108022439

  日期：2008.9.15

  The initial goal of this work was to verify the geometry of the product of a photochemical reaction, viz. the title compound, C8H10O6S, (II). Our crystallographic study firmly establishes the cis-anti-cis nature of the substituents on the cyclobutane ring. The geometry is also designated as exo, where exo signifies that the five-membered ring is on the opposite side of the central cyclobutane ring from the carboxylic acid substituents. The structure determination reveals two molecules, A and B, in the asymmetric unit that display substantially different conformations of the bicyclic core: the cyclobutane ring puckering angles are 22 and 3 degrees, and the sulfolane ring conformations are twist (S-exo) and envelope (S-endo). Intrigued by this variation, we then compared the conformations of other molecules in the Cambridge Structural Database that have sulfolane rings fused to cyclobutane rings. In this class of compound, there are five examples of saturated cyclobutane rings, with ring puckering angles ranging from 3 to 35 degrees. The sulfolane rings were more similar: four of the six molecules exhibit envelope conformations with S-endo, as in molecule B of ( II). Despite the conformational differences, the hydrogen-bonding scheme for both molecules is similar: carboxyl -OH groups form hydrogen bonds with carboxyl and sulfone O atoms. Alternating A and B molecules joined by hydrogen bonds between sulfone O atoms and carboxyl -OH groups form parallel chains that extend in the ac plane. Other hydrogen bonds between the carboxyl groups link the chains along the b axis.