(1,2)-反式-1-羟基-1,2-二氢-2-苯甲酸萘酯 | 359820-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (1,2)-反式-1-羟基-1,2-二氢-2-苯甲酸萘酯
• 英文名称: (1S,2S)-benzoic acid 1-hydroxy-1,2-dihydronaphthalen-2-yl-ester
• 英文别名: (1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl benzoate；(1S,2S)-1,2-Dihydro-1,2-naphthalenediol 2-benzoate；[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl] benzoate
• CAS: 359820-45-4
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: HTGSBYSSVSBBBO-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  1,4-epoxy-1,4-dihydronaphthalene 、 苯甲酸 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (2S,4S)-(-)-2,4-双(二苯基磷)戊烷 、 三乙胺 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.67h， 以95%的产率得到(1,2)-反式-1-羟基-1,2-二氢-2-苯甲酸萘酯
  参考文献：
  名称：

  Rhodium/zinc co-catalyzed asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids

  摘要：

  The asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids are described. By using the complex of [Rh(COD)Cl](2) and (S,S)-BDPP, with ZnI2 as the co-catalyst, a range of aromatic acids and alkyl acids were utilized as nucleophiles to afford the corresponding chiral hydronaphthalene products with high enantioselectivities (84-94% ee). Thus, the present methodology has provides an effective synthetic method for the preparation of enantioenriched hydronaphthalenes. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.11.004

文献信息

• Rhodium-catalysed asymmetric ring opening reactions with carboxylate nucleophiles
  作者：Mark Lautens、Keith Fagnou

  DOI：10.1016/s0040-4020(01)00351-9

  日期：2001.6

  We have developed an asymmetric ring opening reaction of oxabenzonorbornadiene with carboxylate nucleophiles to generate enantiomerically enriched hydronaphthalene products containing an allylic carboxylate moiety. These reactions occur in good yield and excellent enantioselectivity (>90% ee). The allylic carboxylate functionality was found to be stable towards reaction with the rhodium catalyst under

  我们已经开发了氧杂苯并降冰片二烯与羧酸亲核试剂的不对称开环反应，以产生对映异构体富集的含有萘甲酸羧酸酯部分的氢化萘产物。这些反应以高收率和优异的对映选择性（> 90％ee）发生。发现在反应条件下，烯丙基羧酸盐官能团对于与铑催化剂的反应是稳定的。为了获得这些结果，需要两个进步。首先，质子添加剂的使用对于良好的反应性是必要的。第二，需要催化剂上的卤化物配体从氯化物到碘化物的交换以获得高ee。
• Iridium-Catalyzed Asymmetric Ring-Opening of Oxabicyclic Alkenes with Carboxylic Acids
  作者：Yuhua Long、Xiaolu Li、Xuejing Pan、Dandan Ding、Xuan Xu、Xiongjun Zuo、Dingqiao Yang、Sanyong Wang、Chunrong Li

  DOI：10.1007/s10562-013-1136-x

  日期：2014.3

  in 1 followed by SN2′ nucleophilic attack by carboxylic acids. The effects of various bisphosphine ligands, Ag(I) salts, ammonium halides, bases, and solvents on the yields and enantioselectivities of the reaction were also investigated. The theoretical analysis of stability and hydrogen bond for 1-hydroxy-1,2-dihydronaphthalen-2-yl 4-chlorobenzoate 2a were performed using the density functional theory

  报道了一种新颖的铱催化的氧杂二环烯烃与各种羧酸的不对称开环，得到相应的反式羧酸 1-羟基-1,2-二氢-萘-2-基酯产物，产率良好在温和条件下具有中等的对映选择性。反式产物是通过对 1 中桥头碳-氧键的对映选择性裂解，然后是 SN2' 羧酸的亲核攻击形成的。还研究了各种双膦配体、Ag(I) 盐、卤化铵、碱和溶剂对反应产率和对映选择性的影响。使用密度泛函理论B3LYP方法对1-羟基-1,2-二氢萘-2-基4-氯苯甲酸酯2a的稳定性和氢键进行了理论分析。通过X射线衍射分析证实了产物2a的反式构型。提出了目前催化反应的可能机制。 图文摘要报道了一种新型的铱催化的氧杂双环烯烃与多种羧酸的不对称开环，得到相应的反式羧酸 1-羟基-1,2-二氢-naphthalen-2-yl 酯产物在温和条件下具有中等对映选择性，收率良好。反式产物是通过对 1 中桥头碳-氧键的对映选择性裂解，然后是 SN2' 羧酸的
• Rhodium/zinc co-catalyzed asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids
  作者：Xiaobo He、Jingchao Chen、Xin Xu、Fan Yang、Cuiping Gu、Yongyun Zhou、Baomin Fan

  DOI：10.1016/j.tetasy.2016.11.004

  日期：2017.1

  The asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids are described. By using the complex of [Rh(COD)Cl](2) and (S,S)-BDPP, with ZnI2 as the co-catalyst, a range of aromatic acids and alkyl acids were utilized as nucleophiles to afford the corresponding chiral hydronaphthalene products with high enantioselectivities (84-94% ee). Thus, the present methodology has provides an effective synthetic method for the preparation of enantioenriched hydronaphthalenes. (C) 2016 Elsevier Ltd. All rights reserved.