(2S,4S)-5,5-dichloroleucine | 695188-70-6

• 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: (2S,4S)-5,5-dichloroleucine
• 英文别名: (2S,4S)-2-amino-5,5-dichloro-4-methylpentanoic acid
• CAS: 695188-70-6
• 化学式: C₆H₁₁Cl₂NO₂
• 分子量: 200.065
• InChiKey: HFQHHPQIYDQWFY-IMJSIDKUSA-N

物化性质

• 熔点：
  222-223 °C
• 沸点：
  280.6±40.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4S)-5,5-dichloroleucine 在 sodium hydride 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 (2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid
  参考文献：
  名称：

  Total Synthesis of the Chlorinated Marine Natural Product Dysamide B

  摘要：

  [GRAPHICS]Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.

  DOI：

  10.1021/ol062279f
• 作为产物：
  描述：

  (2S,4S)-2-(di(tert-butoxycarbonyl)amino)-4-methyl-6-oxohexanoic acid tert-butyl ester 在 lead(IV) acetate 、 sodium chlorite 、 potassium dihydrogenphosphate 、 N-氯代丁二酰亚胺 、 1,4-环己二烯 、 4 A molecular sieve 、 双氧水 、 叔丁胺 、 三氟乙酸 作用下， 以 四氯化碳 、 水 、 乙腈 、 苯 为溶剂， 反应 9.0h， 生成 (2S,4S)-5,5-dichloroleucine
  参考文献：
  名称：

  Total Synthesis of the Chlorinated Marine Natural Product Dysamide B

  摘要：

  [GRAPHICS]Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.

  DOI：

  10.1021/ol062279f

文献信息

• Stereochemical Assignments of the Chlorinated Residues in Victorin C
  作者：Christine Willis、Amanda Durow、Craig Butts

  DOI：10.1055/s-0029-1216910

  日期：2009.9

  Victorins are cyclic pentapeptide natural products isolated from the fungus Cochliobus victoriae. Using a combination of synthesis and spectroscopic methods we have assigned the geometry of the vinyl chloride residue and determined the stereochemistry of the 5,5-dichloroleucine moiety.

  维克多霉素是从真菌柯氏旋孢腔菌中分离出的环状五肽天然产物。通过结合合成与光谱方法，我们确定了乙烯基氯残基的几何结构，并测定了5,5-二氯亮氨酸部分的立体化学结构。
• Halogenation of Unactivated Carbon Centers in Natural Product Biosynthesis:  Trichlorination of Leucine during Barbamide Biosynthesis
  作者：Danica P. Galonić、Frédéric H. Vaillancourt、Christopher T. Walsh

  DOI：10.1021/ja060151n

  日期：2006.3.1

  The in vitro reconstitution of leucine halogenation during barbamide biosynthesis has been accomplished. It has been demonstrated that the triple chlorination of the unactivated pro-R methyl group of the peptidyl carrier protein-tethered l-Leu substrate is carried out by the tandem action of two nonheme iron(II)-dependent halogenases, BarB1 and BarB2. Investigation of the substrate specificities of

  巴巴胺生物合成过程中亮氨酸卤化的体外重组已经完成。已经证明，肽基载体蛋白束缚的 l-Leu 底物的未活化 pro-R 甲基的三重氯化是通过两种非血红素铁 (II) 依赖性卤化酶 BarB1 和 BarB2 的串联作用进行的。对每种卤化酶的底物特异性的研究揭示了它们在三氯亮氨酸生成中的互补作用。
• A study of polychlorinated leucine derivatives: synthesis of (2S,4S)-5,5-dichloroleucine
  作者：Ana Ardá、Carlos Jiménez、Jaime Rodrı́guez

  DOI：10.1016/j.tetlet.2004.02.118

  日期：2004.4

  The first total synthesis of (2S,4S)-5,5-dichloroleucine has been achieved in 11 steps from L-pyroglutamic acid. A key step is the dichlorination process on the hydrazone of aldehyde 13 with CuCl2 in triethylamine. (C) 2004 Elsevier Ltd. All rights reserved.
• Total Synthesis of the Chlorinated Marine Natural Product Dysamide B
  作者：Amanda C. Durow、G. Cliona Long、Susan J. O'Connel、Christine L. Willis

  DOI：10.1021/ol062279f

  日期：2006.11.9

  [GRAPHICS]Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.