3-异丙基-5-戊内酯 | 56947-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 3-异丙基-5-戊内酯
• 中文别名: (+)-3-异丙基-5-羟基戊酸内酯
• 英文名称: (+/-)-4-isopropyltetrahydropyran-2-one
• 英文别名: 4-Isopropyl-tetrahydro-pyran-2-on；4-(Propan-2-yl)oxan-2-one；4-propan-2-yloxan-2-one
• CAS: 56947-55-8
• 化学式: C₈H₁₄O₂
• mdl: MFCD24503258
• 分子量: 142.198
• InChiKey: YQBZIFFQEPWLLH-UHFFFAOYSA-N

物化性质

• 沸点：
  138 °C(Press: 14 Torr)
• 密度：
  0.973±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  存在于烤烟烟叶、白肋烟烟叶、香料烟烟叶及烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

制备方法与用途

制备方法

• 烟草: BU,56;BU,14;FC,9;FC,OR,BU,18;FC,40。

合成制备方法

• 烟草：BU，56；BU，14；FC，9；FC，OR，BU，18；FC，40。

用途简介

反应信息

• 作为反应物：
  描述：

  3-异丙基-5-戊内酯 在 palladium on activated charcoal 正丁基锂 、 氢气 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 生成 5-(2-Methanesulfonyloxy-ethyl)-2,6-dimethyl-heptanoic acid ethyl ester
  参考文献：
  名称：

  通过分子内酯烯醇化物烷基化反应在环己烷环形成中的折叠应变立体控制

  摘要：

  通过 LDA 处理，研究了 7-溴-2-甲基庚酸乙酯与链中不同位置的附加取代基环化的非对映选择性。

  DOI：

  10.1139/v96-279
• 作为产物：
  描述：

  3-isopropylglutaric anhydride 在 Ru₂Cl₄(DIOP)3 氢气 、 三乙胺 作用下， 以 甲苯 为溶剂， 100.0 ℃ 、980.59 kPa 条件下， 反应 5.0h， 生成 3-异丙基-5-戊内酯
  参考文献：
  名称：

  钌（II）手性膦配合物催化环酸酐的不对称加氢

  摘要：

  通过使用Ru（II）配合物和手性膦配体DIOP作为催化剂，对五元和六元环状酸酐进行氢化，可以获得旋光性γ-和δ-内酯。

  DOI：

  10.1016/s0040-4039(01)82939-7

文献信息

• Catalytic asymmetric hydrogenation of cyclic anhydrides using ruthenium (II) chiral phosphine complex
  作者：Kohtaro Osakada、Masamichi Obana、Takao Ikariya、Masahiko Saburi、Sadao Yoshikawa

  DOI：10.1016/s0040-4039(01)82939-7

  日期：1981.1

  Optically active γ- and δ-lactones are obtained by the hydrogenation of five- and six-membered cyclic anhydrides using a Ru(II) complex with chiral phosphine ligand, DIOP, as a catalyst.

  通过使用Ru（II）配合物和手性膦配体DIOP作为催化剂，对五元和六元环状酸酐进行氢化，可以获得旋光性γ-和δ-内酯。
• FUNCTIONALIZED LONG-CHAIN HYDROCARBON MONO- AND DI-CARBOXYLIC ACIDS AND THEIR USE FOR THE PREVENTION OR TREATMENT OF DISEASE
  申请人：ESPERVITA THERAPEUTICS, INC.

  公开号：US20210024447A1

  公开（公告）日：2021-01-28

  This invention provides compounds of Formulae (IA), (IB), (IC), (ID), (IE), (IF), (IG), (IH), (IJ), (IK), (IL), (II), (III), (IIIA), and (IIIB); pharmaceutically acceptable salts and solvates thereof; and compositions thereof. This invention further provides methods for treating a disease, including but not limited to, liver disease or an abnormal liver condition; cancer (such as hepatocellular carcinoma or cholangiocarcinoma); a malignant or benign tumor of the lung, liver, gall bladder, bile duct or digestive tract; an intra- or extra-hepatic bile duct disease; a disorder of lipoprotein; a lipid-and-metabolic disorder; cirrhosis; fibrosis; a disorder of glucose metabolism; a cardiovascular or related vascular disorder; a disease resulting from steatosis, fibrosis, or cirrhosis; a disease associated with increased inflammation (such as hepatic inflammation or pulmonary inflammation); hepatocyte ballooning; a peroxisome proliferator activated receptor-associated disorder; an ATP citrate lyase disorder; an acetyl-coenzyme A carboxylase disorder; obesity; pancreatitis; or renal disease.

  这项发明提供了Formulae（IA）、（IB）、（IC）、（ID）、（IE）、（IF）、（IG）、（IH）、（IJ）、（IK）、（IL）、（II）、（III）、（IIIA）和（IIIB）的化合物；这些化合物的药学上可接受的盐和溶剂；以及它们的组合物。这项发明还提供了治疗疾病的方法，包括但不限于肝病或异常肝脏状况；癌症（如肝细胞癌或胆管癌）；肺、肝、胆囊、胆管或消化道的恶性或良性肿瘤；肝内或肝外胆管疾病；脂蛋白紊乱；脂质和代谢紊乱；肝硬化；纤维化；葡萄糖代谢紊乱；心血管或相关血管紊乱；由脂肪变性、纤维化或肝硬化引起的疾病；与炎症增加有关的疾病（如肝炎或肺炎炎症）；肝细胞球形变；过氧化物酶体增殖子激活受体相关的疾病；ATP柠檬酸裂合酶疾病；乙酰辅酶A羧化酶疾病；肥胖；胰腺炎；或肾脏疾病。
• Farnesoid X receptor agonists and uses thereof
  申请人：Metacrine, Inc.

  公开号：US10377717B2

  公开（公告）日：2019-08-13

  Described herein are compounds that are farnesoid X receptor agonists, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with farnesoid X receptor activity.

  本文描述了法尼类固醇 X 受体激动剂化合物、制造此类化合物的方法、包含此类化合物的药物组合物和药物，以及使用此类化合物治疗与法尼类固醇 X 受体活性相关的病症、疾病或紊乱的方法。
• Functionalized long-chain hydrocarbon mono- and di-carboxylic acids and their use for the prevention or treatment of disease
  申请人：ESPERVITA THERAPEUTICS, INC.

  公开号：US11084773B1

  公开（公告）日：2021-08-10

  This invention provides compounds of Formulae (IA), (IB), (IC), (ID), (IE), (IF), (IG), (IH), (IJ), (IK), (IL), (II), (III), (IIIA), and (IIIB); pharmaceutically acceptable salts and solvates thereof; and compositions thereof. This invention further provides methods for treating a disease, including but not limited to, liver disease or an abnormal liver condition; cancer (such as hepatocellular carcinoma or cholangiocarcinoma); a malignant or benign tumor of the lung, liver, gall bladder, bile duct or digestive tract; an intra- or extra-hepatic bile duct disease; a disorder of lipoprotein; a lipid-and-metabolic disorder; cirrhosis; fibrosis; a disorder of glucose metabolism; a cardiovascular or related vascular disorder; a disease resulting from steatosis, fibrosis, or cirrhosis; a disease associated with increased inflammation (such as hepatic inflammation or pulmonary inflammation); hepatocyte ballooning; a peroxisome proliferator activated receptor-associated disorder; an ATP citrate lyase disorder; an acetyl-coenzyme A carboxylase disorder; obesity; pancreatitis; or renal disease.

  本发明提供了式(IA)、(IB)、(IC)、(ID)、(IE)、(IF)、(IG)、(IH)、(IJ)、(IK)、(IL)、(II)、(III)、(IIIA)和(IIIB)的化合物；其药学上可接受的盐和溶液；及其组合物。本发明进一步提供了治疗疾病的方法，包括但不限于肝脏疾病或肝脏异常状况；癌症（如肝细胞癌或胆管癌）；肺、肝、胆囊、胆管或消化道的恶性或良性肿瘤；肝内或肝外胆管疾病；脂蛋白紊乱；脂质和代谢紊乱；肝硬化；纤维化；糖代谢紊乱；心血管或相关血管疾病；脂肪变性、纤维化或肝硬化导致的疾病；与炎症（如肝脏炎症或肺部炎症）加重相关的疾病；肝细胞气球化；过氧化物酶体增殖激活受体相关疾病；ATP柠檬酸裂解酶紊乱；乙酰辅酶A羧化酶紊乱；肥胖症；胰腺炎；或肾脏疾病。
• Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor
  作者：Andrea D'Annibale、Laura Ciaralli、Mauro Bassetti、Chiara Pasquini

  DOI：10.1021/jo070600h

  日期：2007.8.1

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.