di-l-menthyl malonate | 73636-64-3

• 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: di-l-menthyl malonate
• 英文别名: (-)-dimenthyl malonate；bis[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] propanedioate
• CAS: 73636-64-3
• 化学式: C₂₃H₄₀O₄
• 分子量: 380.568
• InChiKey: DXIMSSOEQPVPJZ-OKAKVDCISA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  435.2±18.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di-l-menthyl malonate 在 三氟甲烷磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95.7%的产率得到di-(-)-menthyl α,α-dichloromalonate
  参考文献：
  名称：

  Lewis Acid-Mediated Selective Chlorinations of Silyl Enolate

  摘要：

  A new method involving efficient, widely applicable, and highly selective alpha-chlorination of simple silyl enolate with Lewis acid and an alpha,alpha-dichloro-1,3-dicarbonyl controller unit was reported. Diastereoselectivity and enantioselectivity of the reaction were investigated. High reactivity and selectivity were achieved by using alpha,alpha-dichlorinated malonic ester.

  DOI：

  10.1021/ja0454485
• 作为产物：
  描述：

  丙二酸 、 L-薄荷醇 生成 di-l-menthyl malonate
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Hypervalent iodine(III) catalyzed radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes under photolysis
  作者：Sermadurai Selvakumar、Qi-Kai Kang、Natarajan Arumugam、Abdulrahman I. Almansour、Raju Suresh Kumar、Keiji Maruoka

  DOI：10.1016/j.tet.2017.08.018

  日期：2017.10

  bearing (−)-8-phenylmenthol as a chiral auxiliary with aliphatic aldehydes is realized under photolysis. This work represent the first example of diastereoselective addition of acyl radicals to olefins to afford chiral ketones in a highly stereoselective fashion. The reaction is initiated by the photolysis of hypervalent iodine(III) catalyst under mild and metal-free conditions. The synthetic potential

  在光解作用下，实现了带有（-）-8-苯基薄荷醇作为手性助剂的亚烷基丙二酸酯的高价碘（III）催化的非对映选择性自由基加氢酰化。这项工作代表了将酰基非对映选择性加成至烯烃，从而以高度立体选择性的方式得到手性酮的第一个例子。该反应是通过在温和且不含金属的条件下光解高价碘（III）催化剂而引发的。该方法的合成潜力已通过（-）-亚甲基乳酸内酯的短时正式合成得到了证明。
• Trimethylchlorosilane and Silicon Tetrachloride in Two Novel Methodologies for the Efficient and Mild Aldol Addition of β-Keto Esters and Malonates to Aldehydes
  作者：Antonio Massa、Ada Roscigno、Paolo De Caprariis、Rosanna Filosa、Antonia Di Mola

  DOI：10.1002/adsc.201000573

  日期：2010.12.17

  mild aldol additions of β-keto esters and malonates to aldehydes are described using two novel protocols in the presence of silicon tetrachloride and trimethylchlorosilane, respectively. Scope and limitations of the methods have been discussed. Moreover the stability of the obtained products, trimethylsilyl protection of the hydroxy group, as well as the role of both silicon tetrachloride and trimethylchlorosilane

  描述了分别在四氯化硅和三甲基氯硅烷存在下使用两种新颖的方法将β-酮酸酯和丙二酸酯高效和温和地添加到醛中的方法。已经讨论了方法的范围和局限性。此外，还分析了所得产物的稳定性，羟基的三甲基甲硅烷基保护以及四氯化硅和三甲基氯硅烷在获得最终产物中的作用。
• Synthesis and Reactivity of the 3-Substituted Isoindolinone Framework to Assemble Highly Functionalized Related Structures
  作者：Carmen Petronzi、Selene Collarile、Gianluca Croce、Rosanna Filosa、Paolo De Caprariis、Antonella Peduto、Laura Palombi、Valentina Intintoli、Antonia Di Mola、Antonio Massa

  DOI：10.1002/ejoc.201200678

  日期：2012.9

  potassium carbonate-catalyzed synthesis of 3-substituted isoindolinones through tandem aldol/cyclization reactions of active methylene compounds with 2-cyanobenzaldehyde is described. The utility of the obtained isoindolinones has been demonstrated through an exploration of the chemical space by employing a series of interesting methodologies that led to diverse, highly functionalized compounds. Among them

  描述了通过活性亚甲基化合物与 2-氰基苯甲醛的串联羟醛/环化反应，高效碳酸钾催化合成 3-取代异吲哚啉酮。所获得的异吲哚啉酮的效用已经通过对化学空间的探索通过一系列有趣的方法得到证明，这些方法导致了多样化的、高度官能化的化合物。其中，令人惊讶的直接碳酸钾催化的双串联反应导致了三环半胺醛衍生物。
• Living Cyclopolymerization of 1,6-Heptadiyne Derivatives Using Well-Defined Alkylidene Complexes: Polymerization Mechanism, Polymer Structure, and Polymer Properties
  作者：Harold H. Fox、Michael O. Wolf、Richard O'Dell、Beatrice L. Lin、Richard R. Schrock、Mark S. Wrighton

  DOI：10.1021/ja00086a016

  日期：1994.4

  Mo(NAr)(CHCMe[sub 2]Ph)(OR[sub F6])[sub 2] (1a; Ar = 2,6-i-Pr[sub 2]C[sub 6]H[sub 3], OR[sub F6] = OCMe(CF[sub 3])[sub 2]) as the initiator in 1,2-dimethoxyethane (DME). The polymers show a high degree of conjugation ([lambda][sub max] > 500 nm) and have narrow molecular weight distributions. Poly(2a) is soluble in most organic solvents (THF, C[sub 6]H[sub 6], toluene, CH[sub 2]Cl[sub 2], CHCl[sub 3], DME

  我们在这里报告了使用明确定义的亚烷基配合物作为引发剂的 1,6-庚二炔衍生物（通常为 4,4-二取代）的活性环聚合。二炔丙基丙二酸二乙酯 (2a)、二炔丙基丙二酸二叔丁基酯 (2b)、旋光二-(1R,2S,5R)-([减])-二炔丙基丙二酸薄荷酯 (2c([减]))、二-(1S, 2R,5S)-(+)-二炔丙基丙二酸薄荷酯 (2c(+)), di-(1R)-endo-(+)-fenyl二炔丙基丙二酸酯 (2d), 4,4-bis[[(p-tolylsulfonyl) oxy]甲基]-1,6-庚二炔 (3b)、4,4-双[(三甲基甲硅烷氧基)甲基]-1,6-庚二炔 (3c)、环状甲硅烷基醚、PhEtSi(OCH[sub 2])[sub 2] C-(CH[sub 2]C[三键]CH)[sub 2] (3d) 和 N,N-二炔丙基-2,4,6-三异丙基苯甲酰胺 (5b) 使用Mo(NAr)(CHCMe[sub
• Regioselective Preparation of Functionalized exo-Methylene- cyclopentanes and exo-Methylenepyrrolidines via Silaborative Carbocyclization of 1,6-Enynes
  作者：Martin Gerdin、Sailendra Kumar Nadakudity、Christin Worch、Christina Moberg

  DOI：10.1002/adsc.201000434

  日期：2010.10.4

  The vinylboronate functions were employed in palladium-catalyzed Suzuki cross-coupling reactions with a range of aryl bromides, containing electron-withdrawing as well as electron-donating substituents, furnishing arylated exo-methylenecyclopentanes or exo-methylenepyrrolidines in good yields. Subsequent oxidation of the isopropoxydimethylsilyl function generated via addition of (chlorodimethylsilyl)pinacolborane

  Pd-PEPPSI-IPr PEPPSI =吡啶增强的前催化剂制剂的稳定和引发；使用（二甲基苯基甲硅烷基）频哪烷硼烷或（氯二甲基甲硅烷基）频哪烷硼烷的IPr ＝N，N-双[2，6-（二异丙基）苯基]咪唑鎓}以优异的收率提供了以单一非对映体的形式进入稠密官能化的五元环的途径。所述vinylboronate功能是在钯-催化的Suzuki交叉偶联与一系列芳基溴化物的反应，含吸电子以及供电子取代基，芳基化家具采用外切-methylenecyclopentanes或外-亚甲基吡咯烷具有良好的收率。通过添加（氯二甲基甲硅烷基）频哪烷硼烷而产生的异丙氧基二甲基甲硅烷基官能团的随后氧化提供了与芳基化化合物的羟甲基衍生物的接触。使用手性酯二（2-丙烯基）（2-丙炔基）丙二酸二薄荷酯，可分离出两种非对映体产物，从而使环化化合物成为单一异构体，在新形成的立体中心具有相反的绝对构型。