(1R,2S)-2-((E)-2-(thiophen-3-yl)vinyl)-1,2-dihydronaphthalen-1-ol | 1338601-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: (1R,2S)-2-((E)-2-(thiophen-3-yl)vinyl)-1,2-dihydronaphthalen-1-ol
• 英文别名: 2-((E)-2-(thiophen-3-yl)vinyl)-1,2-dihydronaphthalen-1-ol
• CAS: 1338601-45-8
• 化学式: C₁₆H₁₄OS
• 分子量: 254.353
• InChiKey: SSNGRYWHTVHGNO-QNQFUXMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-((E)-2-(thiophen-3-yl)vinyl)-1,2-dihydronaphthalen-1-ol 在 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 以69%的产率得到(1R,2S)-2-(2-(thiophen-3-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes

  摘要：

  An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intra-molecular Friedel Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.

  DOI：

  10.1021/jo201781x
• 作为产物：
  描述：

  1,4-epoxy-1,4-dihydronaphthalene 、 E-2-(噻吩-3-基)乙烯基硼酸频那醇酯 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以100%的产率得到(1R,2S)-2-((E)-2-(thiophen-3-yl)vinyl)-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes

  摘要：

  An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intra-molecular Friedel Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.

  DOI：

  10.1021/jo201781x

文献信息

• <scp>Cobalt‐Catalyzed</scp> Enantioselec tive <scp>Ring‐Opening</scp> Reactions of Oxa‐ and Aza‐bicyclic Alkenes with Alkenylboronic Acids
  作者：Di Zhu、Yongmei Zhao、Qinglei Chong、Fanke Meng

  DOI：10.1002/cjoc.202100622

  日期：2022.1.15

  Catalytic enantioselective ring-opening of oxa- and aza-bicyclic alkenes with readily available accessible alkenylboronic acids, promoted by a chiral phosphine–Co complex, is reported. Such a process represents the unprecedented Co-catalyzed introduction of various alkenyl groups onto the oxa- and aza-bicyclic alkenes, affording a wide range of multisubstituted functionalized cyclohexenes in up to

  据报道，在手性膦-钴配合物的促进下，氧杂和氮杂双环烯烃与容易获得的烯基硼酸催化对映选择性开环。这样的过程代表了前所未有的将各种烯基引入氧杂-和氮杂-双环烯烃上，以高达 98% 的收率和 99.5:0.5 er 提供范围广泛的多取代官能化环己烯。