(+)-p-menth-3-ylchloride | 104012-59-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-p-menth-3-ylchloride
• 英文别名: (-)-menthyl chloride；Cyclohexane, 2-chloro-4-methyl-1-(1-methylethyl)-, (1R,2S,4S)-rel-；(1R,2S,4S)-2-chloro-4-methyl-1-propan-2-ylcyclohexane
• CAS: 104012-59-1
• 化学式: C₁₀H₁₉Cl
• 分子量: 174.714
• InChiKey: OMLOJNNKKPNVKN-AEJSXWLSSA-N

物化性质

• 沸点：
  216.1±9.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (+)-p-menth-3-ylchloride 在 lithium 作用下， 以 正戊烷 为溶剂， 生成 menthane-1-carboxylic acid
  参考文献：
  名称：

  Cyclohexylmetal compounds. II. Nuclear magnetic resonance and carbonation results on (+-)-menthyllithium

  摘要：

  DOI：

  10.1021/jo01269a062
• 作为产物：
  描述：

  L-薄荷醇 在 盐酸 、 zinc(II) chloride 作用下， 以 水 为溶剂， 反应 5.0h， 以95%的产率得到(+)-p-menth-3-ylchloride
  参考文献：
  名称：

  乙烯基芳烃的催化不对称加氢烯基化：底物和手性N-杂环碳烯配体的电子效应

  摘要：

  乙烯基芳烃与末端烯烃的不对称尾到尾交叉氢化烯基化反应是通过催化带有手性N-杂环卡宾（NHC）的NiH配合物实现的。该反应提供了具有高对映选择性（最高94％ee）和化学选择性（交叉/均产物比：最高99：1）的支链宝石-二取代烯烃 。NHC配体的乙烯基芳烃和N-芳基上的取代基的电子效应（但不是π，π堆积机制）有助于空间效应并影响交叉氢化烯基化的结果。

  DOI：

  10.1002/anie.201411882

文献信息

• Zinc-Mediated Hydroxyallylation of Aldehydes with Cyclopropanols: Direct Access to Vicinal <i>anti</i>-<i>sec</i>,<i>tert</i>-Diols via Enolized Homoenolates
  作者：Yoshiya Sekiguchi、Naohiko Yoshikai

  DOI：10.1021/acs.orglett.1c04331

  日期：2022.1.28

  by zinc-mediated α-hydroxyallylation of aldehydes with cyclopropanols. The reaction features the action of the zinc-enolized homoenolate as a γ-oxyallyl nucleophile toward the carbonyl electrophile. The diastereoselectivity of the present reaction is ascribed to the strong preference for a chelated (Z)-configuration of the enolized homoenolate as well as the bicyclic chairlike transition state it forms

  通过锌介导的醛与环丙醇的α-羟基烯丙基化反应，可以直接和非对映选择性地合成邻位抗-sec、叔二醇。该反应的特点是锌烯醇化高烯醇化物作为 γ-氧烯丙基亲核试剂对羰基亲电试剂的作用。本反应的非对映选择性归因于对烯醇化均烯醇化物的螯合（Z）构型的强烈偏好以及它与醛形成的双环椅状过渡态，其中醛取代基更倾向于占据准轴位置。
• [EN] 3-SUBSTITUTED PARA-MENTHANE DERIVATIVES<br/>[FR] DÉRIVÉS DE PARA-MENTHANE 3-SUBSTITUÉS
  申请人：GIVAUDAN SA

  公开号：WO2014009416A1

  公开（公告）日：2014-01-16

  A compound of formula (I), wherein the symbol, formula (II), represents a double bond when X is an oxygen atom or a single bond when X is a hydroxyl group, and Y represents a hydrogen atom or a substituent in the meta or para position, the substituent if present being hydroxyl, CN or -CH2CN, useful as a cooling compound.

  式（I）的化合物，其中符号，式（II），当X为氧原子时表示双键，当X为羟基时表示单键，Y表示氢原子或间位或对位的取代基，如果存在取代基，则为羟基，CN或-CH2CN，可用作冷却剂。
• Enantioselective catalysis. Part 119: New chiral 2-(2-pyridinyl)oxazoline ligands containing an additional optically active substituent in the pyridine system
  作者：Henri Brunner、Reinhard Störiko、Bernhard Nuber

  DOI：10.1016/s0957-4166(97)00619-8

  日期：1998.2

  The synthesis of novel chiral nitrogen ligands and their precursors is described. They consist of an optically active oxazoline bound to pyridine in the 2-position. In addition, another optically active substituent is attached to the pyridine ring. The effect of the two independent stereogenic units in one ligand was studied in the Rh(I)-catalysed enantioselective hydrosilylation of acetophenone with

  描述了新型手性氮配体及其前体的合成。它们由在2位上结合吡啶的旋光性恶唑啉组成。另外，另一个光学活性取代基连接到吡啶环上。在Rh（I）催化的苯乙酮与二苯基硅烷的对映选择性氢化硅烷化反应中，研究了一个配体中两个独立的立体生成单元的作用。
• A synthetic approach to the cis-fused marine pyranopyrans, (3E)- and (3Z)-dactomelyne. X-ray structure of a rare organomercurial
  作者：Alan P. Kozikowski、Jaemoon Lee

  DOI：10.1021/jo00290a014

  日期：1990.2
• Synthesis and characterization of chiral (-)-menthyltin(IV) compounds. X-ray structure of tert-butyl-8-(dimethylamino)naphthyl-(-)-menthyltin hydride
  作者：Herbert Schumann、Birgit C. Wassermann、F. Ekkehardt Hahn

  DOI：10.1021/om00044a019

  日期：1992.8

  A series of optically active (-)-menthyltin(IV) derivatives with tin directly bound to a chiral carbon atom has been synthesized and characterized. The Grignard reagent derived from (-)-menthyl chloride stereospecifically reacts with trimethyltin chloride to afford (-)-menthyltrimethyltin (1). 1 is derivatized by selective bromodemetalation, alkylation, and hydrogenation, yielding (-)-menthyldimethyltin bromide (2), tert-butyl-(-)-menthyldimethyltin (3), tert-butyl-(-)-menthyltin dibromide (4), and each prochiral at the tin center as well as tert-butyl-8-(dimethylamino)naphthyl-(-)-menthyltin bromide (5) and hydride (6), in which an additional center of asymmetry has been created at the tin atom. By means of multinuclear NMR investigations, the conformation of the optically active ligand in 1-6 was determined, the coordination behavior of the potentially bidentate aminonaphthyl ligand in 5 and 6, resulting in a trigonal bipyramidal (5) or a distorted tetrahedral (6) structure in solution, was established, and for 5 and 6, the ratio of epimers differing in the absolute configuration at the tin center was determined to be 45:55 and 40:60, respectively. The single-crystal X-ray structural analysis of 6 revealed a pair of R(Sn)/S(Sn) epimers. 6 crystallizes monoclinically, space group P2(1), with a = 17.786 (8) angstrom, b = 10.890 (4) angstrom, c = 13.700 (8) angstrom, beta = 108.0 (4)-degrees, and Z = 4. The structure was solved from 4449 observed reflections with I greater-than-or-equal-to 3-sigma(I) and refined to a final R factor of 0.028. The coordination geometry around tin for the two molecules in the asymmetric unit is that of a trigonal bipyramidal-like monocapped tetrahedron showing a very weak Sn-N interaction with a Sn-N distance of 2.931 (3) (molecule A) or 2.885 (3) angstrom (molecule B). The Sn-H bond lengths are 1.52 (5) and 1.63 (5) angstrom, respectively.