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: bis(5-methyl-2-propan-2-ylcyclohexyl) propanedioate；racem.-dimenthyl malonate；racem.-Malonsaeure-dimenthylester；racem.-Dimenthyl-malonat；Malonsaeure-bis<(1R)-menthyl>ester；di-(1S,2R,5S)-(+)-menthyl malonate；di-d-menthyl malonate；di-d-menthylmalonate；di-((1S)-menthyl)-malonate；Malonsaeure-di-((1S)-menthylester)
• CAS: 73636-64-3；131348-66-8；141611-48-5
• 化学式: C₂₃H₄₀O₄
• 分子量: 380.568
• InChiKey: DXIMSSOEQPVPJZ-QHOCJJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 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：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  di-l-menthyl malonate 在 三氯硅烷 、 三乙胺 、 sodium t-butanolate 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of Cyclic 1,2‐Bisphosphines by Tandem Michael Addition of 2,3‐Bis(diarylphosphinyl)‐1,3‐butadiene

  摘要：

  AbstractA base‐promoted tandem Michael addition of malonates to 2,3‐ bis(diarylphosphinyl)‐1,3‐butadienes was developed for the synthesis of cyclopentyl 1,2‐bisphosphine compounds. This method enables rapid construction of various 1,2‐bis(diarylphosphinyl)cyclopentanes, and features readily accessible reactants, mild conditions and good functional group tolerance. The product could be easily transformed to the corresponding transition metal complexes, which may find broad applications in asymmetric catalysis.

  DOI：

  10.1002/ejoc.202201257
• 作为产物：
  描述：

  D-薄荷醇 在 丙酮 作用下， 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

• 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
• Asymmetrische Totalsynthese von 19-Nor-Steroiden mit photochemischer Schlüsselreaktion: Enantiomerenreine Zielverbindungen
  作者：Gerhard Quinkert、Ulrich Schwartz、Herbert Stark、Wolf-Dietrich Weber、Friedhelm Adam、Helmut Baier、Gudrun Frank、Gerd Dürner

  DOI：10.1002/jlac.198219821109

  日期：1982.11.22

  Eine Totalsynthese der enantiomerenreinen 19-Nor-Steroide Östron (1a), 19-Norandrost-4-en-3,17-dion (2a), östradiol-17β (3a) und 19-Nortestosteron (4a) wird beschrieben. Sie folgt dem A + DADABCD-Aufbauprinzip, durchläuft ein lichtinduziertes, kinetisch instabiles o-Chinodimethan-Derivat und verwendet den chiralen Synthesebaustein (R)-2-Vinyl-1,1-cyclopropan-dicarbonsäure-dimethylester (12b). 12b ist

  描述了对映体纯的19- nor-类固醇雌酮（1a），19-norandrost-4-en-3,17-dione（2a），雌二醇-17β（3a）和19-nortestosterone（4a）的全合成。它遵循A + DADABCD的构建原理，通过光诱导的，动力学上不稳定的邻二醌甲烷衍生物，并使用手性合成构件（R）-2-乙烯基-1,1-环丙烷-二羧酸二甲酯（12b） 。通过不对称诱导的S cN'反应可以容易地接近图12b（见图2）。在合成中，以对映体纯的形式获得12b。分析程序表明在每种情况下，12b具有光学纯度或对映体过量95％。
• Synthesis of enantiomerically pure C2-branched-2-deoxy-heptitols
  作者：Antonio Saba、Victor Adovasio、Mario Nardelli

  DOI：10.1016/s0957-4166(00)86062-0

  日期：1992.12

  2,3; 4,5-Di-O-isopropylidene-al-L-(+)-arabinose la reacts with di-l-menthylmalonate to give the hepturonates 2a and 3a in a manno-gluco 7.8:2.2 ratio. The C-2 branched2-Deoxy-2-hydroxy-methyl-L-manno-heptitol 6 and 2-Deoxy-2-hydroxy-methyl-L-gluco-heptitol 7 were obtained by submitting 2a and 3a to routine procedures. When the same reaction was performed with di-d-menthylmalonate a 3.5:6.5 mixture of 2b and 3b was obtained. A 8.2:1.8 anti-diastereoselectivity was also observed by reacting 2,3;4,5-O-tetraacetyl-al-D-(-)-arabinose 1b with di-d-menthylmalonate. The absolute stereochemistry of the major hepturonate 10 obtained in this reaction was secured hy a single crystal X-ray analysis.
• Katagiri, Nobuya; Haneda, Toru; Watanabe, Nobuhisa, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 10, p. 3867 - 3877
  作者：Katagiri, Nobuya、Haneda, Toru、Watanabe, Nobuhisa、Hayasaka, Etsuko、Kaneko, Chikara

  DOI：——

  日期：——
• A simple stereoselective synthesis of C2-branched 2-deoxy-pentitols.
  作者：Antonio Saba

  DOI：10.1016/s0957-4166(00)80278-5

  日期：1992.1

  2,3-O-isopropylidene-D(+)-glyceraldehyde reacts with di-l-menthyl-malonate to give the penturonates 2a, and 3a in an erythro-threo 8.5:1 ratio. The C2-branched sugars 2-deoxy-2-hydroxymethyl-3,4-erythro-pentitol 6 and 2-deoxy-2-hydroxymethyl-3,4-threo-pentitol 7 were obtained by submitting 2a and 3a to routine procedures. The same reaction, performed with di-d-menthylmalonate, resulted in a decreased diastereoselectivity, providing a 2.5:1 mixture of erythro and threo diastereomers.