5-(cyclohex-1-en-1-yl)benzo[d][1,3]dioxole | 90867-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(cyclohex-1-en-1-yl)benzo[d][1,3]dioxole
• 英文别名: 5-(Cyclohex-1-en-1-yl)-2H-1,3-benzodioxole；5-(cyclohexen-1-yl)-1,3-benzodioxole
• CAS: 90867-76-8
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: WFMKXQUMEOFRPL-UHFFFAOYSA-N

物化性质

• 沸点：
  310.8±42.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(cyclohex-1-en-1-yl)benzo[d][1,3]dioxole 在 sodium hydroxide 、 potassium hexamethyldisilazane 、 双氧水 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 生成 (3S,3aR,7aS)-3a-Benzo[1,3]dioxol-5-yl-3-hydroxy-hexahydro-benzofuran-2-one
  参考文献：
  名称：

  Synthesis of .alpha.-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines

  摘要：

  DOI：

  10.1021/jo00191a048
• 作为产物：
  描述：

  4-溴-1,2-亚甲二氧基苯 在 叔丁基锂 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 5-(cyclohex-1-en-1-yl)benzo[d][1,3]dioxole
  参考文献：
  名称：

  通过质子耦合电子转移实现对映选择性光氧化还原催化：不对称氮杂-频哪醇环化的发展

  摘要：

  报道了第一个用于酮和腙还原偶联的高度对映选择性催化方案。这些反应通过由手性磷酸催化剂和光氧化还原催化剂 Ir(ppy)2(dtbpy)PF6 共同介导的协同质子耦合电子转移 (PCET) 事件产生的中性羰基自由基中间体进行。值得注意的是，在随后的 CC 键形成步骤过程中，这些中性羰基自由基似乎保持与布朗斯台德酸的手性共轭碱 H 键合，从而提供具有优异水平的非对映选择性和对映选择性的顺式 1,2-氨基醇衍生物. 这项工作首次证明了不对称催化中协同 PCET 活化的可行性和潜在益处。

  DOI：

  10.1021/ja4100595

文献信息

• Arylation and Vinylation of Alkenes Based on Unusual Sequential Semipinacol Rearrangement/Grob Fragmentation of Allylic Alcohols
  作者：Dao-Yi Yuan、Yong-Qiang Tu、Chun-An Fan

  DOI：10.1021/jo801434b

  日期：2008.10.3

  Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation.

  通过有趣的NBS促进的半频哪醇重排以及随后的异常NaOH介导的Grob裂解，烯烃可以在温和的条件下进行立体选择性芳基化和乙烯基化，而无需使用过渡金属催化剂。
• Regioselective Annulation of Alicyclic−Aromatic Dienes with 3-Halo-3-cyclobutene-1,2-diones. Synthesis of Annulated α-Halobenzocyclobutenones¹
  作者：Arthur H. Schmidt、Gunnar Kircher、Elmar Bräu

  DOI：10.1021/jo971948n

  日期：1998.3.1

  4-(1-Cycloalken-1-yl)-1,2-dialkoxybenzenes 8, 10, and 11 and 5-(1-cycloalken-1-yl)-1,3-benzodioxoles 12-15 react with the semisquaric halides 5a and 5b in a dehydrative annulation process to give the annulated alpha-halobenzocyclobutenones 9a,b and 16a,b-21a,b in poor to good yields (20-76%). The reaction failed with alicyclic-aromatic dienes having no or only one alkoxy group in the benzene ring. The dehydrative annulation process could be extended to 4-(3,4-dimethoxyphenyl)-1,2-dihydronaphthalene (24), affording the highly annulated alpha-chlorobenzocyclobutenone 25 in 50% yield. In the case of 5-(1-cyclobuten-1-yl)-1,3-benzodioxole (22), reaction with the semisquaric halides 5a,b yielded the dicyclobutanaphthodioxole-1,2-dione (23) as the sole product in a dehydrochlorinative annulation process. A reaction pathway has been suggested for the dehydrative annulation process. Several of the annulated alpha-halobenzocyclobutenones prepared were submitted to selected chemical transformations. Thus, the reaction with tributyltin hydride afforded the annulated benzocyclobutenones 26a-f in excellent yields (74-78%), and treatment with silver trifluoroacetate afforded the alpha-(trifluoroacetoxy)benzocyclobutenones 27a-c in 71-79% yields.
• DAVIS, F. A.;VISHWAKARWA, LAL, C.;FINN, J.;BILLWERS, J. M., J. ORG. CHEM., 1984, 49, N 17, 3241-3243
  作者：DAVIS, F. A.、VISHWAKARWA, LAL, C.、FINN, J.、BILLWERS, J. M.

  DOI：——

  日期：——
• JPH04321636A
  申请人：——

  公开号：JPH04321636A

  公开（公告）日：1992-11-11
• Stereoconvergent Approach to the Enantioselective Construction of α‐Quaternary Alcohols by Radical Epoxide Allylation
  作者：Sebastian Höthker、Annika Plato、Stefan Grimme、Zheng-Wang Qu、Andreas Gansäuer

  DOI：10.1002/anie.202405911

  日期：——

  Abstract: We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α‐quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)‐promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all carbon quaternary stereocenters in a unique fashion.