3-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-3-oxopropanoic acid | 53943-72-9

• 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: 3-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-3-oxopropanoic acid
• 英文别名: 3-(menthyloxy)-3-oxopropanoic acid；menthoxycarbonylacetic acid；((1R)-menthyl)-hydrogenmalonate；Malonsaeure-mono-((1R)-menthylester)；((1R)-Menthyl)-hydrogenmalonat；(-)-Carbomenthoxyessigsaeure；3-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3-oxopropanoic acid
• CAS: 53943-72-9
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: FQELCANCOKLAGK-OUAUKWLOSA-N

物化性质

• 沸点：
  355.9±25.0 °C(Predicted)
• 密度：
  1.0238 g/cm3(Temp: 69.6 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-3-oxopropanoic acid 在 氯化亚砜 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  手性（-）-薄荷基的位置对联苯-苯甲酸酯液晶中蓝相形成和中间相行为的影响

  摘要：

  八种新的手性液晶化合物4-（4- menthyloxy- Ñ -oxoalkanoyloxy）联苯-4'-基4- butoxybenzoates中号Ñ B4OB（Ñ  = 1-8）中，通过修改的位置制备手性（ - ） -薄荷基通过逐渐增加二羧酸间隔基的烷基链长度来使基于薄荷醇的液晶化合物中的芳族化合物有效。所有化合物均通过FT-IR和NMR光谱进行表征，以证明其化学结构。进行了差示扫描量热法（DSC），偏振光学显微镜（POM）和X射线衍射，系统地研究了它们的相变行为。手性（-）-薄荷基相对于核心的位置对BP的形成和同构行为有很大影响。仅CLC具有短间隔链的M 1 B4OB和M 2 B4OB呈现蓝色相。此外，柔性间隔物的长度和奇偶性对相结构和相变行为具有深远的影响。对于这些手性液晶化合物，观察到奇偶效应。

  DOI：

  10.1016/j.molliq.2019.112003
• 作为产物：
  描述：

  di-l-menthyl malonate 在 sodium hydroxide 作用下， 生成 3-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-3-oxopropanoic acid
  参考文献：
  名称：

  Abbot; Christie; McKenzie, Chemische Berichte, 1938, vol. 71, p. 9,15

  摘要：

  DOI：

文献信息

• Access to Unprotected β-Fluoroalkyl β-Amino Acids and Their α-Hydroxy Derivatives
  作者：Volodymyr Sukach、Serhii Melnykov、Sylvain Bertho、Iryna Diachenko、Pascal Retailleau、Mykhailo Vovk、Isabelle Gillaizeau

  DOI：10.1021/acs.orglett.9b00622

  日期：2019.4.5

  β-(het)aryl-β-fluoroalkyl β-amino acids and their α-hydroxy derivatives can be readily obtained using a decarboxylative Mannich-type reaction without protection/deprotection steps. This protocol utilizes lithium hexamethyldisilazide and (het)arylfluoroalkyl ketones to generate NH-ketimine intermediates. The mild reaction conditions allow the preparation of original fluorinated β-amino acids as useful building

  使用脱羧曼尼希型反应可容易地获得未保护的β-（杂）芳基-β-氟代烷基β-氨基酸及其α-羟基衍生物，而无需保护/脱保护步骤。该协议利用六甲基二硅叠氮化锂和（杂）芳基氟烷基酮生成NH-酮亚胺中间体。温和的反应条件允许以实用且可扩展的方式将原始的氟化β-氨基酸制备为有用的结构单元。
• One-pot tethering of organic molecules through non-symmetric malonate derivatives
  作者：Daniel Sherman、Rimma Shelkov、Artem Melman

  DOI：10.1016/j.tetlet.2005.05.044

  日期：2005.7

  A new method for one-pot chemoselective beterobifunctional cross-linking of organic molecules is described. The method is based on tert-butyldiphenylsilyl malonate and involves two sequential carbodiimide couplings with two different molecules possessing a hydroxy or an amino functionality with one intermediate one-pot fluoride deprotection. (c) 2005 Elsevier Ltd. All rights reserved.
• Modulation of doxorubicin activity in cancer cells by conjugation with fatty acyl and terpenyl hydrazones
  作者：K. Effenberger、S. Breyer、R. Schobert

  DOI：10.1016/j.ejmech.2010.01.037

  日期：2010.5

  Doxorubicin N-acylhydrazones derived from saturated, unsaturated and terpene-terminated fatty acids were tested for anticancer activity in cells of human HL-60 leukaemia, 518A2 melanoma, MCF-7/Topo breast and KB-V1/Vbl cervix carcinomas. In the latter, the N-heptadecanoyl hydrazone was more cytotoxic than its unsaturated C(18)-fatty acyl analogues and even three times more than doxorubicin. The (menthoxycarbonyl)undecanoyl hydrazone was twice as active as doxorubicin in these multidrug resistant KB-V1/Vbl and in the 518A2 cells and also more efficacious in KB-V1 and MCF-7 cells that had been desensitised for doxorubicin. All hydrazones induced apoptosis albeit by slightly different mechanisms. While apoptosis induction by the menthoxymalonyl hydrazone was characterized by an upfront increase in caspase-8 activity, all other hydrazones elicited a hike in caspase-9 activity. Treatment of HL-60 and 518A2 cells with doxorubicin or its heptadecanoyl, linolenoyl, (menthoxycarbonyl)undecanoyl or menthoxymalonyl hydrazones also led to diverging increases of the ratio of bax to bcl-2 mRNA expression, of reactive oxygen species and of mitochondrial membrane damage. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Stereochemical studies. XV. Ferrocene studies. XXII. Planar elements of stereochemistry
  作者：Stanley I. Goldberg、William D. Bailey

  DOI：10.1021/ja00827a022

  日期：1974.10
• The effect of the position of chiral (−)-menthyl on the formation of blue phase and mesophase behavior in biphenyl-benzoate liquid crystals
  作者：Zhang-Pei Chen、Xin-Jiao Wang、Ling-Xin Meng、Ji-Wei Wang、Ying-Gang Jia

  DOI：10.1016/j.molliq.2019.112003

  日期：2020.1

  Eight new chiral liquid crystal compounds 4-(4-menthyloxy-n-oxoalkanoyloxy) biphenyl-4′-yl 4-butoxybenzoates MnB4OB (n = 1–8), were prepared by modifying the position of chiral (−)-menthyl in the menthol based liquid crystal compounds through gradually increasing the alkyl chain length of the dicarboxylic spacer. All compounds were characterized by FT-IR and NMR spectroscopy in order to prove their

  八种新的手性液晶化合物4-（4- menthyloxy- Ñ -oxoalkanoyloxy）联苯-4'-基4- butoxybenzoates中号Ñ B4OB（Ñ  = 1-8）中，通过修改的位置制备手性（ - ） -薄荷基通过逐渐增加二羧酸间隔基的烷基链长度来使基于薄荷醇的液晶化合物中的芳族化合物有效。所有化合物均通过FT-IR和NMR光谱进行表征，以证明其化学结构。进行了差示扫描量热法（DSC），偏振光学显微镜（POM）和X射线衍射，系统地研究了它们的相变行为。手性（-）-薄荷基相对于核心的位置对BP的形成和同构行为有很大影响。仅CLC具有短间隔链的M 1 B4OB和M 2 B4OB呈现蓝色相。此外，柔性间隔物的长度和奇偶性对相结构和相变行为具有深远的影响。对于这些手性液晶化合物，观察到奇偶效应。