3-benzylcyclohex-2-en-1-ol | 201021-72-9

• 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-benzylcyclohex-2-en-1-ol
• CAS: 201021-72-9
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: ZYEJVKQYFBBJQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-benzylcyclohex-2-en-1-ol 在 sodium chlorite 、 sodium hydride 、 碳酸氢钠 、 sodium phosphate 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 萘烷 为溶剂， 生成 Spiro[2,4-dihydronaphthalene-3,3'-cyclohexene]-1-one
  参考文献：
  名称：

  Synthesis and evaluation of spirobenzazepines as potent vasopressin receptor antagonists

  摘要：

  A novel series of spirobenzazepines was synthesized and evaluated for V-1a and V-2 receptor antagonist activity. Compounds 8b, 8i, and 8k have shown selective V-1a receptor antagonist activity. Compounds 8p and 8q were shown to be dual V-1a/V-2 receptor antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.103
• 作为产物：
  描述：

  苄基溴化镁 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-benzylcyclohex-2-en-1-ol
  参考文献：
  名称：

  Synthesis and evaluation of spirobenzazepines as potent vasopressin receptor antagonists

  摘要：

  A novel series of spirobenzazepines was synthesized and evaluated for V-1a and V-2 receptor antagonist activity. Compounds 8b, 8i, and 8k have shown selective V-1a receptor antagonist activity. Compounds 8p and 8q were shown to be dual V-1a/V-2 receptor antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.103

文献信息

• Progressive Studies on the Novel Samarium-Catalyzed Diastereoselective Tandem Semipinacol Rearrangement/Tishchenko Reduction of Secondaryα-Hydroxy Epoxides
  作者：Chun-An Fan、Xiang-Dong Hu、Yong-Qiang Tu、Bao-Min Wang、Zhen-Lei Song

  DOI：10.1002/chem.200304782

  日期：2003.9.22

  A novel and highly diastereoselective samarium-catalyzed tandem rearrangement/reduction of secondary alpha-hydroxy epoxides, which involves a C1 to C3 carbon migration rearrangement and a very interesting hetero-Tishchenko reduction of the intermediate aldehyde and the reductant aldehyde, has been reported. This reaction could be developed to provide a facile and stereoselective construction of 2-quarternary

  已经报道了新颖且高度非对映选择性的mar催化的串联α-羟基环氧化物的重排/还原，其涉及从C1至C3的碳迁移重排以及中间醛和还原性醛的非常有趣的异-Tishchenko还原。可以发展该反应以提供具有连接至非对映异构季碳中心的羟甲基部分的2-季铵1，3-二醇单元的简便且立体选择性的构造。已经进行了有关醛作为还原剂的筛选，反应条件的优化以及该串联反应的底物范围的详细研究。此反应的催化循环，还原性醛的电子和空间效应以及1的酰基迁移的机理
• A novel AlEt3-promoted tandem reductive rearrangement of 1-benzyloxy-2,3-epoxides: new route to 2-quaternary 1,3-diol unitsElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b2/b209948a/
  作者：De Run Li、Wu Jiong Xia、Yong Qiang Tu、Fu Min Zhang、Lei Shi

  DOI：10.1039/b209948a

  日期：2003.3.6

  A novel and highly stereoselective tandem rearrangement-reduction reaction of 1-benzyloxy-2,3-epoxide, under the promotion of triethylaluminum (AlEt3), has been developed to construct a quaternary stereocenter and the hydroxymethyl attached to the carbon center in one-step.

  在三乙基铝 (AlEt3) 的促进下，1-苄氧基-2,3-环氧化物的新型高立体选择性串联重排还原反应，一步构建了季立体中心和连接到碳中心的羟甲基.
• Regio- and Stereoselective Addition of HO/OOH to Allylic Alcohols
  作者：Xiao-Tao Wang、Wei-Bo Han、Hui-Jun Chen、Qinghong Zha、Yikang Wu

  DOI：10.1021/acs.joc.0c01280

  日期：2020.8.7

  readily react with ethereal H2O2 in the presence of catalytic amounts of Na2MoO4-gly or MoO2(acac)2, affording the C═C trans hydroxylation–hydroperoxylation products in good yields with high regio- and stereoselectivity. Use of enantiomers of cyclic substrates resulted in corresponding enantiopure diol-tert-hydroperoxides. The possibility of further conversion of the diol-tert-hydroperoxides into triols

  在催化量的Na 2 MoO 4 -gly或MoO 2（acac）2的存在下，一系列烯丙醇易于与醚H 2 O 2反应，从而以高收率提供C═C反羟基化-氢过氧化产物具有高区域选择性和立体选择性。使用环状底物的对映异构体产生相应的对映体纯的二醇-叔氢过氧化物。还举例说明了将二醇-叔氢过氧化物进一步转化为具有包含季中心的分离的叔-过氧基团的三醇或线性结构单元的可能性。
• A Structural-Reporter Group to Determine the Core Conformation of Sialyl Lewisx Mimetics
  作者：Beatrice Wagner、Florian P. C. Binder、Xiaohua Jiang、Tobias Mühlethaler、Roland C. Preston、Said Rabbani、Martin Smieško、Oliver Schwardt、Beat Ernst

  DOI：10.3390/molecules28062595

  日期：——

  The d-GlcNAc moiety in sialyl Lewisx (sLex, 1) acts predominantly as a linker to position the d-Gal and the l-Fuc moieties in the bioactive spatial orientation. The hypothesis has been made that the NHAc group of GlcNAc pushes the fucose underneath the galactose and, thus, contributes to the stabilization of the bioactive conformation of the core of sLex (1). To test this hypothesis, GlcNAc mimetics

  唾液酸 Lewisx (sLex, 1) 中的 d-GlcNAc 部分主要充当接头，以在生物活性空间方向上定位 d-Gal 和 l-Fuc 部分。假设 GlcNAc 的 NHAc 基团将岩藻糖推到半乳糖下方，从而有助于稳定 sLex 核心的生物活性构象 (1)。为了检验这一假设，合成了由 (R,R)-1,2-环己二醇取代的 GlcNAc 模拟物，这些取代物被与岩藻糖部分连接位置相邻的烷基和芳基取代基取代。为了探索广泛的扩展和空间要求高的 R 基团，应用了一种用于合成 3-烷基/芳基-1,2-环己二醇 (3b-n) 的酶促方法。这些环己二醇衍生物被并入 sLex 模拟物 2b-n。为了分析亲和力和核心构象的关系，应用了 1 H NMR 结构报告基团概念。因此，H-C5Fuc 的化学位移被证明是此类 sLex 模拟物核心预组织程度的敏感指标，因此可用于量化 R 基团的贡献。
• Chemo-enzymatic preparation of optically active endo-bicyclo[4.1.0]heptan-2-ols
  作者：Jean-Pierre Barnier、Véronique Morisson、Isabelle Volle、Luis Blanco

  DOI：10.1016/s0957-4166(99)00099-3

  日期：1999.3

  Resolutions of endo-bicyclo[4.1.0]heptan-2-ols were achieved by acylation in the presence of lipase from Candida antarctica (Novozym(R)). The (1S,2R,6R) enantiomers reacted faster and the enantiomeric ratios were between 60 and 800 for the 6-substituted bicycloalkanols. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.