2-Allyl-3-dimethylbuttersaeure | 25015-42-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Allyl-3-dimethylbuttersaeure
• 英文别名: 2-tert-butylpent-4-enoic acid
• CAS: 25015-42-3
• 化学式: C₉H₁₆O₂
• mdl: MFCD20643657
• 分子量: 156.225
• InChiKey: ISDQHACGSZQURY-UHFFFAOYSA-N

物化性质

• 沸点：
  88-92 °C(Press: 6 Torr)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Allyl-3-dimethylbuttersaeure 在 sodium azide 、 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 磷酸二丁酯 、 对苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 (±)-(4R,5R)-4-(tert-butyl)-5-vinyloxazolidin-2-one
  参考文献：
  名称：

  N-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation

  摘要：

  A Pd(II)/bis-sulfoxide/Bronsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and pi-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.

  DOI：

  10.1021/ja506036q
• 作为产物：
  描述：

  diethyl allyl t-butylmalonate 生成 2-Allyl-3-dimethylbuttersaeure
  参考文献：
  名称：

  Synthese de .DELTA.-lactones. V. Synthese d'alcoyl-3 .DELTA.-lactones.

  摘要：

  通过溴代烯丙烷的缩合，然后通过烷基卤化物与乙基丙二酸酯反应，我们制备了乙基烷基烯丙基丙二酸酯。这些酯的水解产生烷基-2Δ4-戊烯酸，利用双（3-甲基-2-丁基）硼烷，将其转化为烷基-2-羟基-5-戊酸。这些羟基酸的环化脱水反应产生烷基-3-δ-内酯。

  DOI：

  10.1248/cpb.24.538

文献信息

• [EN] GAMMA-AMINOAMIDE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] MODULATEURS GAMMA-AMINOAMIDES DE L'ACTIVITE DE RECEPTEUR DE CHIMIOKINE
  申请人：MERCK & CO INC

  公开号：WO2004041279A1

  公开（公告）日：2004-05-21

  The present invention is directed to compounds of the formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R11, R12, W, X, and n are defined herein, which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.

  本发明涉及式(I)的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、R11、R12、W、X和n在此处定义，这些化合物可用作趋化因子受体活性的调节剂。特别是，这些化合物可用作趋化因子受体CCR-2的调节剂。
• Palladium-Catalyzed Allylic Alkylation of Doubly Deprotonated Carboxylic Acids
  作者：Manfred Braun、Panos Meletis、Robin Visse

  DOI：10.1002/adsc.201100372

  日期：2011.12

  Doubly deprotonated carboxylic acids undergo smooth palladium-catalyzed carbon alkylations with the allylic substrates methyl allyl carbonate and (E)-methyl (pent-3-en-2-yl) carbonate to give γ,δ-unsaturated carboxylic acids. A diastereoselective and enantioselective protocol leads to (2S,3R)-hexenoic acid in 87% ee.

  双去质子化的羧酸与烯丙基底物碳酸甲基烯丙酯和（E）-甲基（戊-3-烯-2-基）碳酸酯进行平滑的钯催化的碳烷基化反应，得到γ，δ-不饱和羧酸。非对映选择性和对映选择性方案导致87％ee中的（2 S，3 R）-己酸。
• Trialkylamine-Mediated Intramolecular Acylation of Akenes with Carboxylic Acid Chlorides
  作者：Jun-ichi Matsuo、Takaya Hoshikawa、Shun Sasaki、Hiroyuki Ishibashi

  DOI：10.1248/cpb.58.591

  日期：——

  Trialkylamine-mediated intramolecular cyclization of pent-4-enoyl chlorides was studied. Substitution with a tertiary alkyl group at the 2-position gave cyclopent-2-en-1-ones, while substitution with an aromatic group gave enol esters, which were formed by O-acylation of initially formed 3-chlorocyclopentanones with ketenes.

  研究了三烷基胺介导的戊-4-烯酰氯分子内环化。在 2 位用叔烷基取代可得到环戊-2-烯-1-酮，而用芳香基取代可得到烯醇酯，烯醇酯是由最初形成的 3-氯环戊酮与烯酮发生 O-酰化反应而形成的。
• Aminolactonization of Unactivated Alkenes Catalyzed by Aryl Iodine
  作者：Lu-Wen Zhang、Xiao-Jun Deng、Dong-Xu Zhang、Qin-Qin Tian、Wei He

  DOI：10.1021/acs.joc.1c00074

  日期：2021.4.2

  protocol of the aryl iodine-catalyzed aminolactonization of unactivated alkenes under oxidation conditions was first reported to efficiently construct diverse amino lactones in a short time using HNTs2 as the compatible nitrogen source. In addition, we investigated the influence of the reaction rate based on the structure of the iodoarene precatalyst, which revealed the selective adjustment effect on aminolactonization

  首次报道了在氧化条件下芳基碘催化未活化烯烃的氨基内酯化的一步协议，可使用HNTs 2作为相容氮源在短时间内有效构建各种氨基内酯。此外，我们基于碘芳烃预催化剂的结构研究了反应速率的影响，揭示了对氨基内酯化和氧内酯化的选择性调节作用。最后，初步实验验证了手性碘芳烃预催化剂催化不对称氨基内酯化的可行性。
• Gamma-aminoamide modulators of chemokine receptor activity
  申请人：Butora Gabor

  公开号：US20050261325A1

  公开（公告）日：2005-11-24

  The present invention is directed to compounds of the formula (1), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , W, X, and n are defined herein, which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.

  本发明涉及公式（1）化合物，其中R1，R2，R3，R4，R5，R6，R7，R8，R11，R12，W，X和n在此定义，这些化合物可用作趋化因子受体活性调节剂。特别地，这些化合物可用作趋化因子受体CCR-2的调节剂。