(S)-4-(羟甲基)环己烯 | 5681-56-1

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-4-(羟甲基)环己烯
• 中文别名: 1-环己-3-烯基甲醇；螺旋-周线-螺旋蛋白质m-β
• 英文名称: (S)-1-(3-Cyclohexenyl)methanol
• 英文别名: (S)-4-(Hydroxymethyl)cyclohexene；(1S)-cyclohex-3-enemethanol；(S)-4-Hydroxymethyl-cyclohexen；S(-)-3-Cyclohexen-1-methanol；(S)-3-cyclohexene-1-methanol；[(1S)-cyclohex-3-en-1-yl]methanol
• CAS: 5681-56-1；1679-51-2；5709-99-9；72581-32-9
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: VEIYJWQZNGASMA-SSDOTTSWSA-N

物化性质

• 沸点：
  190-192 °C (lit.) 80-85 °C/18 mmHg (lit.)
• 密度：
  0.961 g/mL at 25 °C (lit.)
• 闪点：
  169 °F
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）
• LogP：
  1.500 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

制备方法与用途

用途：重要有机中间体；医药中间体

反应信息

• 作为反应物：
  描述：

  (S)-4-(羟甲基)环己烯 以 吡啶 、 二甲基亚砜 为溶剂， 反应 3.5h， 生成 (1S)-cyclohex-3-eneacetonitril
  参考文献：
  名称：

  摘要：

  Cyclic nucreo-delta-amino acids that constitute monomers of a conformationally constrained nucleo-delta-peptide base-pairing system have been prepared. Their synthesis starts with an enantioselectively catalyzed chirogenic Diels-Alder reaction, proceeds via a regioselective epsilon-iodolactamization process, and ends with a regio- as well as diastereoselective introduction of nucleobases through S(N)2-type opening of a transiently formed N-acylaziridine ring. Extensive use of X-ray crystal-structure analysis has been made to support structure assignments.

  DOI：

  10.1002/1522-2675(20000607)83:6<1049::aid-hlca1049>3.0.co;2-1
• 作为产物：
  描述：

  3-环己烯-1-甲酸 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (S)-4-(羟甲基)环己烯
  参考文献：
  名称：

  Ceder,O.; Hansson,B., Acta Chemica Scandinavica (1947), 1970, vol. 24, # 8, p. 2693 - 2698

  摘要：

  DOI：

文献信息

• Enantioselective Synthesis of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation: A Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds
  作者：Taigang Zhou、Byron Peters、Matías F. Maldonado、Thavendran Govender、Pher G. Andersson

  DOI：10.1021/ja306731u

  日期：2012.8.22

  A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Bäcklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up

  开发了一种高效且对映选择性 Ir 催化的不饱和砜加氢反应。以优异的对映选择性（高达 98% ee）生产手性环状和无环砜。与 Ramberg-Bäcklund 重排相结合，该反应提供了一种获得具有优异对映选择性（高达 97% ee）和高产率（高达 94%）的手性烯丙基和同型烯丙基化合物的新途径。
• Amino acid derivatives having renin inhibiting activity
  申请人：Hoffmann La Roche Inc.

  公开号：US05688946A1

  公开（公告）日：1997-11-18

  The compounds of the formula ##STR1## in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diastereomeric racemates as well as pharmaceutically usable salts thereof inhibit the activity of the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations in the control or prevention of high blood pressure and cardiac insufficiency.

  上述化学公式##STR1##的化合物，以光学纯的立体异构体、立体异构体混合物、立体异构体对映体混合物或立体异构体对映体混合物的形式，以及它们的药用盐，都能抑制天然酶肾素的活动，因此可以以药物制剂的形式用于控制或预防高血压和心功能不全。
• Camphor-DerivedN-Acryloyl andN-Crotonoyl Sultams: Practical Activated Dienophiles in AsymmetricDiels-alder Reactions. Preliminary Communication
  作者：Wolfgang Oppolzer、Christian Chapuis、G�rald Bernardinelli

  DOI：10.1002/hlca.19840670527

  日期：1984.8.8

  Starting from (+)-camphor-10-sulfonyl chloride (5), the crystalline sultam 8 was easily prepared. Lewis-acid-promoted Diels-Alder additions of the crystalline N-acry-loyl and N-crotonoyl derivatives 9 and 10, respectively, to cyclopentadiene and 1,3-butadiene at −130 to −78° furnished adducts 11, 12 and 17 with high chiral efficiency. Crystallization of the adducts and nondestructive removal of 8 gave

  从（+）-樟脑-10-磺酰氯（5）开始，容易制得结晶阿片8。路易斯-酸-促进的狄尔斯-阿尔德结晶的添加Ñ -acry-loyl和Ñ -crotonoyl衍生物9和10，分别向环戊二烯和在-130 1,3-丁二烯至-78°布置的加合物11，12和17具有高手性效率。所述加合物和非破坏性拆卸的结晶8，得到任一醇13，14和18 IR酸19％的对映体纯度为19。在使用8的对映异构体作为辅助剂时，诱导的感觉相反。通过X射线衍射分析确定了10的结构。
• Practical AsymmetricDiels-Alder Additions to Camphor-10-sulfonic-Acid-Derived Acrylates. Preliminary Communication
  作者：Wolfgang Oppolzer、Christian Chapuis、Martha J. Kelly

  DOI：10.1002/hlca.19830660747

  日期：1983.11.2

  Starting from (+)-camphor-10-sulfonic acid (1) the chiral crystalline alcohols 3 and 11 were prepared in two steps. Lewis-acid-mediated [4+2]-additions of their acrylates to 1,3-dienes were studied. Notably, the crystalline acrylate 4 underwent TiCl2 (OiPr)2-promoted Diels-Alder addition to cyclopentadiene giving after recrystallization efficiently the pure (2R)-adduct 5.

  从（+）-樟脑-10-磺酸（1）开始，分两步制备手性结晶醇3和11。研究了路易斯酸介导的丙烯酸酯向[1,3-二烯]的[4 + 2]加成反应。值得注意的是，在重结晶后，结晶的丙烯酸酯4经受了环戊二烯的TiCl 2（OiPr）2促进的Diels - Alder加成，从而有效地提供了纯的（2 R）加合物5。
• A Diruthenium Catalyst for Selective, Intramolecular Allylic C–H Amination: Reaction Development and Mechanistic Insight Gained through Experiment and Theory
  作者：Mark Edwin Harvey、Djamaladdin G. Musaev、J. Du Bois

  DOI：10.1021/ja203576p

  日期：2011.11.2

  tetrakis(2-oxypyridinato)diruthenium(II,III) chloride, [Ru(2)(hp)(4)Cl], catalyzes intramolecular allylic C-H amination with bis(homoallylic) sulfamate esters. These results stand in marked contrast to reactions performed with dirhodium catalysts, which favor aziridine products. The following discussion constitutes the first report of C-H amination using complexes such as [Ru(2)(hp)(4)Cl] and related diruthenium adducts

  混合价桨轮复合物四 (2-oxypyridinato) diruthenium (II,III) 氯化物 [Ru(2)(hp)(4)Cl]，催化分子内烯丙基 CH 胺化与双（高烯丙基）氨基磺酸酯。这些结果与使用有利于氮丙啶产物的铱催化剂进行的反应形成鲜明对比。以下讨论构成了使用复合物如 [Ru(2)(hp)(4)Cl] 和相关二钌加合物的 CH 胺化的第一份报告。计算和实验研究涉及 [Ru(2)(hp)(4)Cl] 促进的 CH 胺化的机制，涉及氢原子提取/自由基重组和离散但短命的双自由基物种的中介。集体数据为理解这种催化剂氧化烯丙基（和苄基）CH 键的偏好提供了一个连贯的模型。