[3,4-Dimethylidene-6-(4-methylphenyl)sulfonyloxyhexyl] 4-methylbenzenesulfonate | 185899-63-2

• 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: [3,4-Dimethylidene-6-(4-methylphenyl)sulfonyloxyhexyl] 4-methylbenzenesulfonate
• CAS: 185899-63-2
• 化学式: C₂₂H₂₆O₆S₂
• 分子量: 450.577
• InChiKey: WWSXNMBNCNXNKS-UHFFFAOYSA-N

物化性质

• 沸点：
  614.0±55.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3,4-Dimethylidene-6-(4-methylphenyl)sulfonyloxyhexyl] 4-methylbenzenesulfonate 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 25.5h， 生成 1,1-dichloro-9-methylene-6-azaspiro[2,6]non-6-yl-p-tolylsulfone
  参考文献：
  名称：

  8,11-Dichloro-N-tosyl-3-aza[5]metacyclophane:  A Highly Strained Aromatic System

  摘要：

  DOI：

  10.1021/ja9634987
• 作为产物：
  描述：

  diethyl 3,4-dimethylenehexanedioate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 [3,4-Dimethylidene-6-(4-methylphenyl)sulfonyloxyhexyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  铜催化的脱氢狄尔斯-阿尔德反应

  摘要：

  的实用而有效的铜催化脱氢Diels-Alder反应宝石-diesters和与二烯烃酮已经建立。通过基于自由基的脱氢过程原位产生活性二烯亲和体，其与多种二烯反应，以良好或优异的收率得到各种多取代的环己烯衍生物。

  DOI：

  10.1021/acs.orglett.8b01067

文献信息

• Synthesis of Cyclic Allylborates from 1,3‐Dienes and a Diboron Reagent
  作者：Seiya Sakuragi、Tomofumi Akiba、Takumi Tanahashi、Tetsuaki Fujihara

  DOI：10.1002/anie.202202226

  日期：2022.6.13

  The synthesis of cyclic allylborates was achieved by the reaction of 1,3-dienes and B2pin2 using a copper catalyst. The cyclic allylborate could be used in several organic transformations such as regioselective protonation, the allylation of electrophiles, and Suzuki–Miyaura coupling.

  环状烯丙基硼酸盐的合成是通过 1,3-二烯和 B 2 pin 2使用铜催化剂反应来实现的。环状烯丙基硼酸盐可用于多种有机转化，例如区域选择性质子化、亲电试剂的烯丙基化和 Suzuki-Miyaura 偶联。
• Synthesis of constrained α-amino acid derivatives via Diels-Alder approach
  作者：Sambasivarao Kotha、Enugurthi Brahmachary、Nampally Sreenivasachary

  DOI：10.1016/s0040-4039(98)00562-0

  日期：1998.6

  Synthesis of new five and seven membered outer ring diene building blocks containing alpha-amino acid moiety and their usage in the preparation of the constrained amino acid derivatives is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of benzocycloheptene-based amino acid derivatives via a [4+2] cycloaddition reaction as a key step
  作者：Sambasivarao Kotha、Nampally Sreenivasachary、Enugurthi Brahmachary

  DOI：10.1016/s0040-4020(01)00575-0

  日期：2001.7

  The seven-membered diene 5 is prepared from 2-butyne-1,4-diol using double orthoester Claisen rearrangement reaction as a key step. The Diels-Alder reaction of the diene 5 with various dienophiles followed by oxidation delivered the benzocycloheptene-based a-amino acid derivatives in very good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Van Es, Daniel S.; Van Eis, Maurice J.; N'krumah, Stephen, Heterocycles, 2001, vol. 54, # 2, p. 799 - 824
  作者：Van Es, Daniel S.、Van Eis, Maurice J.、N'krumah, Stephen、Gret, Norbert、Egberts, Arnet、De Rijke, Marianne、De Kanter, Franciscus J.J.、De Wolf, Willem H.、Bickelhaupt, Friedrich、Spek, Anthony L.

  DOI：——

  日期：——
• Synthesis and anomalous structure–reactivity relationship of 8,11-dichloro[5]metacyclophan-3-one
  作者：Daniël S van Es、Norbert Gret、Marianne de Rijke、Maurice J van Eis、Franciscus J.J de Kanter、Willem H de Wolf、Friedrich Bickelhaupt、Stephan Menzer、Anthony L Spek

  DOI：10.1016/s0040-4020(01)00239-3

  日期：2001.4

  The synthesis, structural characterisation, and reactivity of the title compound are reported. It was prepared in order to investigate the effects of incorporation of an sp(2)-centre in the bridge of a [5]metacyclophane on its structure and reactivity. An X-ray crystal structure of the cyclophanone demonstrates that the benzene ring is distorted to the same extent as in the hydrocarbon parent compound, while there is less strain in the bridge. Nevertheless, the cyclophanone displays a reduced reactivity in Diels-Alder reactions, which is tentatively ascribed to transition state effects. Calculations indicate that in spite of the close proximity between the ketone functionality and the benzene ring, there are no pi-pi interactions between them. (C) 2001 Elsevier Science Ltd. All rights reserved.