methyl 4-methylenecyclohexane carboxylate | 71092-50-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 4-methylenecyclohexane carboxylate
• 英文别名: methyl 4-methylidenecyclohexane-1-carboxylate
• CAS: 71092-50-7
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: SYRKANZKKKAWNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-methylenecyclohexane carboxylate 在 sodium iodide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.0h， 生成 1,1-difluorospiro[2.5]octane-6-carboxylic acid
  参考文献：
  名称：

  官能化的二氟环丙烷的合成：药物发现的独特组成部分

  摘要：

  由功能化烯烃和TMSCF 3 / NaI合成了用于药物发现的含二氟环丙烷的结构单元。获得了新颖的氟化酸，胺，氨基酸，醇，酮和磺酰氯。

  DOI：

  10.1002/chem.201705708
• 作为产物：
  描述：

  三甲基(2-亚甲基丁-3-烯基)硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 4-methylenecyclohexane carboxylate
  参考文献：
  名称：

  Tandem Transformations Involving Allylic Silanes. 2. Highly Diastereoselective Substitutions Involving [(Trialkylsilyl)methyl]cyclohexene Derivatives with Aldehydes. Synthetic Studies on the Problem of Lewis Acid-Promoted Protodesilylation and Enolization

  摘要：

  Diels-Alder cycloaddition of 2-[(trialkylsilyl)methyl]-1,3-butadienes with a variety of dienophiles and substitution reactions between these allylsilane-containing adducts and aldehyde or acid chloride electrophiles have been combined into ''tandem sequential reactions.'' These tandem sequences proceed with equal or greater yield (50-80%) than the reactions performed separately with no decrease in regio- or stereoselectivity. The sequence produces cyclic compounds with three or four stereogenic centers with good to excellent diastereoselectivity from three simple, noncyclic, and achiral reaction partners. Unprecedented levels of diastereoselectivity (de > 93%) have been achieved in allylic substitution reactions involving substituted [(trialkylsilyl)methyl]cyclohexene derivatives with aldehyde electrophiles. During the course of these studies, protodesilylation of allylsilanes has been investigated in detail, and a cocatalyst system of TiCl4 and Me2AlCl has been developed that has eliminated silicon loss in the substitution reactions studied. Lewis acid-promoted enolization of ester and ketone substrates with chiral centers adjacent to the carbonyl moiety has been studied also. It has been shown that this event in our studies occurs primarily during catalyst quench. This isomerization is prevented by quenching the catalyst with a Lewis base, such as methanol or triethylamine, prior to aqueous workup.

  DOI：

  10.1021/jo970821v

文献信息

• 4-Amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function
  作者：Daniel Lednicer、Philip F. VonVoigtlander、D. Edward Emmert

  DOI：10.1021/jm00136a010

  日期：1981.4

  modification of the carbonyl function of analgesics derived from 4-(dimethylamino)-4-arylcyclohexan-1-one was studied by reduction and by addition of nucleophiles. The resulting amino alcohols were separated and assigned structures on the basis of X-ray crystallography, NMR, and TLC mobility. The trans (OH and N) isomers were invariably more potent than the cis. Inclusion of flat lipophilic moieties (phenyl

  通过还原和添加亲核试剂，研究了对衍生自4-（二甲氨基）-4-芳基环己-1-酮的镇痛药的羰基官能团修饰的影响。分离得到的氨基醇，并基于X射线晶体学，NMR和TLC迁移率确定结构。反式（OH和N）异构体总是比顺式更有效。在距含碳羟基至少两个碳原子的距离处包含平坦的亲脂性部分（苯基，环己烯基）导致效力增加了几个数量级。讨论了其对受体相互作用的可能意义。
• LIQUID CRYSTAL COMPOUNDS OF BUTYLENES
  申请人：Hu Baohua

  公开号：US20110260106A1

  公开（公告）日：2011-10-27

  A nematic phase liquid crystal compound with negative dielectric constant has a structure represented by wherein R1 represents a hydrogen atom or linear alkyl having 1 to 8 carbon atoms or linear alkenyl having 1-8 carbon atoms, or an alkoxy or alykenoxy formed by substituting one or nonadjacent two CH1 in the linear alkyl or alkenyl with oxygen atom, wherein 0 to 4 hydrogen atoms of R1 group can be substituted with fluorine; R2 represents a hydrogen atom or linear alkyl having 1 to 8 carbon atoms, or R2 represents a linear fluoroalkyl having 1 to 8 carbon atoms, in which group 0 to 4 hydrogens can be substituted with fluorine atoms; A represents a benzene ring or 1,4-cyclohexane ring, if A is a benzene ring 0 to 4 hydrogen atoms on the benzene ring may be substituted with fluorine; n=1 to 2, and m=0 to 2.

  一种具有负介电常数的向列相液晶化合物，其结构表示为其中，R1代表氢原子或具有1至8个碳原子的线性烷基或具有1至8个碳原子的线性烯基，或通过将线性烷基或烯基中的一个或非相邻的两个CH1取代为氧原子而形成的烷氧基或烯氧基，其中R1基团的0至4个氢原子可以被氟取代；R2代表氢原子或具有1至8个碳原子的线性烷基，或R2代表具有1至8个碳原子的线性氟代烷基，其中该基团的0至4个氢原子可以被氟原子取代；A代表苯环或1,4-环己烷环，如果A是苯环，则苯环上的0至4个氢原子可以被氟取代；n=1至2，m=0至2。
• Reverse hydroxamic acid derivatives
  申请人：——

  公开号：US20040242928A1

  公开（公告）日：2004-12-02

  Reverse hydroxamic acid derivatives having specific structure represented by a general formula (Ia): 1 (wherein A is a hydrogen atom or the like; Ar 1 is an arylene or the like; Ar 2 is an optionally substituted aryl, a heteroaryl or the like; R 1 is a hydrogen atom, an alkyl or the like; R 2a is a substituted cycloaryl, a heterocycloaryl or the like) and a general formula (I): 2 (wherein A, Ar 1 , Ar 2 , and R 1 are the same as defined above and R 2 is an hydrogen atom, R 2a or the like) and salts thereof, which have TNF-&agr; converting enzyme (TACE) inhibitory activity.

  具有特定结构的反式羟胺酸衍生物，通式（Ia）表示如下：1（其中A是氢原子或类似物；Ar1是芳烃或类似物；Ar2是可选取代的芳基、杂环芳基或类似物；R1是氢原子、烷基或类似物；R2a是取代的环烷基、杂环环烷基或类似物），以及通式（I）2（其中A、Ar1、Ar2和R1的定义与上述相同，而R2是氢原子、R2a或类似物），以及其盐，具有TNF-α转化酶（TACE）抑制活性。
• [EN] PYRAZOLO FUSED RING COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ À CYCLE CONDENSÉ PYRAZOLE ET SON UTILISATION<br/>[ZH] 吡唑并环化合物及其应用
  申请人：[en]MEDSHINE DISCOVERY INC.;[zh]南京明德新药研发有限公司

  公开号：WO2023083200A1

  公开（公告）日：2023-05-19

  一类吡唑并环化合物及其应用，具体公开了式(IV)所示化合物及其药学上可接受的盐。
• REVERSE HYDROXAMIC ACID DERIVATIVES
  申请人：KAKEN PHARMACEUTICAL CO., LTD.

  公开号：EP1431285B1

  公开（公告）日：2009-01-07