5,5-Dichlorohexanal | 165260-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-Dichlorohexanal
• CAS: 165260-19-5
• 化学式: C₆H₁₀Cl₂O
• 分子量: 169.051
• InChiKey: HRYAOODZAIZDHF-UHFFFAOYSA-N

物化性质

• 沸点：
  209.1±30.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,5-Dichlorohexanal 在 三氟甲磺酸二丁硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 生成 [(2S,3S)-1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-7,7-dichloro-2-methyl-1-oxooctan-3-yl] 4-nitrobenzoate
  参考文献：
  名称：

  Total Synthesis of Hectochlorin

  摘要：

  [GRAPHIC]Hectochlorin (1) is a marine natural product with significant fungicidal activity. A synthesis effort was initiated to develop a flexible route to hectochlorin which would allow access to analogues with potentially improved activity and/or attributes relative to the natural product. A successful total synthesis of hectochlorin is described.

  DOI：

  10.1021/ol025604h
• 作为产物：
  描述：

  6,6-Dichloro-1-heptene 在 臭氧 、 溶剂黄146 、 锌 作用下， 生成 5,5-Dichlorohexanal
  参考文献：
  名称：

  Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis

  摘要：

  Dolabellin (1), a novel cytotoxic metabolite which consists of two thiazole hydroxy acids and a new dichlorinated beta-hydroxy acid, was isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated on the basis of spectral data in conjunction with chemical degradations, which provided three methyl esters: methyl 2-(1-hydroxy-2 -methylpropyl)thiazole-4-carboxylate (2), methyl 2-(1,2-dihydroxyethyl)thiazole-4-carboxylate (3), and methyl 7,7-dichloro-3-hydroxy-2-methyloctanoate (4). The absolute stereochemistry of 1 was determined by stereoselective syntheses of two degradation products 2 and 3 and two diastereomeric octanoates 7a,b (the dechloro derivatives of degradation product 4), and the enantioselective total synthesis of dolabellin itself. Dechlorodolabellin (23) was also synthesized.

  DOI：

  10.1021/jo00120a021

文献信息

• First Total Synthesis of 27-Deoxylyngbyabellin A
  作者：Yi Liu、Yuguo Du、Yang Zhang

  DOI：10.1055/a-1478-9088

  日期：2021.8

  In this study, we document the first total synthesis of the marine cyanobacteria secondary metabolite 27-deoxylyngbyabellin A in 10 linear steps with 9.7% overall yield. Key steps entailed (1) one-pot cascade reaction of (S)-2-(benzyloxy)-3-methylbutanoic acid and of Boc-l-Ile-OH with a β-azido disulfide building block to access two critical thiazole units, (2) chiral oxazaborolidinone-mediated asymmetric

  在这项研究中，我们记录了海洋蓝细菌次级代谢产物27-deoxylyngbyabellin A的第一个全合成，该合成以10个线性步骤进行，总收率为9.7％。关键步骤包括（1）（S）-2-（苄氧基）-3-甲基丁酸和Boc-1-Ile-OH与β-叠氮基二硫键的一锅级联反应，以访问两个关键的噻唑单元， （2）手性草氮杂硼硼烷酮介导的不对称醛醇缩合反应以构建（S）-β-羟基酯，以及（3）二苯叠氮磷酸酯介导组装的线性前体的大内酰胺化，从而获得天然产物27-脱氧lyngbyabellin A.
• Total syntheses of lyngbyabellins A and B, potent cytotoxic lipopeptides from the marine cyanobacterium Lyngbya majuscula
  作者：Fumiaki Yokokawa、Hirofumi Sameshima、Daichi Katagiri、Toyohiko Aoyama、Takayuki Shioiri

  DOI：10.1016/s0040-4020(02)01224-3

  日期：2002.11

  The first total syntheses of lyngbyabellins A and B, Lyngbya majuscula derived lipopeptides, are described. The functionalized thiazole carboxylic acid units were prepared by the oxidative dehydrogenation of the corresponding thiazolidines with chemical manganese dioxide. The asymmetric synthesis of the dichlorinated β-hydroxy acid by a chiral oxazaborolidinone mediated aldol reaction. Finally, fragment

  描述了Lyngbyabellins A和B，Mascrula majuscula衍生的脂肽的第一次总合成。通过用化学二氧化锰对相应的噻唑烷进行氧化脱氢来制备官能化的噻唑羧酸单元。通过手性草氮杂硼烷酮介导的羟醛反应不对称合成二氯化β-羟基酸。最后，片段缩合，随后进行大内酰胺化，得到了lyngbyabellinA。lyngbyabellinB的总合成是通过在大内酰胺化后形成敏感的噻唑啉环来完成的。
• Total synthesis of lyngbyabellin A, a potent cytotoxic metabolite from the marine cyanobacterium Lyngbya majuscula
  作者：Fumiaki Yokokawa、Hirofumi Sameshima、Takayuki Shioiri

  DOI：10.1016/s0040-4039(01)00678-5

  日期：2001.6

  The first total synthesis of lyngbyabellin A, a novel peptolide from the marine cyanobacterium Lyngbya majuscula, is described. Both functionalized thiazole carboxylic acid units were synthesized using our CMD (chemical manganese dioxide) oxidation from the corresponding thiazolidines. The asymmetric synthesis of the dichlorinated β-hydroxy acid was achieved by the chiral oxazaborolidinone mediated

  描述了lyngbyabellin A的第一个全合成，这是一种来自海洋蓝藻Lyngbya majuscula的新型肽。使用我们的CMD（化学二氧化锰）氧化，从相应的噻唑烷中合成了两个官能化的噻唑羧酸单元。二氯代β-羟基酸的不对称合成是通过手性草氮杂硼烷酮介导的羟醛反应实现的。最后，片段缩合，然后进行大内酰胺化，得到了lyngbyabellinA。
• Total Synthesis of Hectochlorin
  作者：Jeannie R. P. Cetusic、Frederick R. Green、Paul R. Graupner、M. Paige Oliver

  DOI：10.1021/ol025604h

  日期：2002.4.1

  [GRAPHIC]Hectochlorin (1) is a marine natural product with significant fungicidal activity. A synthesis effort was initiated to develop a flexible route to hectochlorin which would allow access to analogues with potentially improved activity and/or attributes relative to the natural product. A successful total synthesis of hectochlorin is described.
• Dolabellin, a Cytotoxic Bisthiazole Metabolite from the Sea Hare Dolabella auricularia: Structural Determination and Synthesis
  作者：Hiroki Sone、Takashi Kondo、Minoru Kiryu、Hiroyuki Ishiwata、Makoto Ojika、Kiyoyuki Yamada

  DOI：10.1021/jo00120a021

  日期：1995.7

  Dolabellin (1), a novel cytotoxic metabolite which consists of two thiazole hydroxy acids and a new dichlorinated beta-hydroxy acid, was isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was elucidated on the basis of spectral data in conjunction with chemical degradations, which provided three methyl esters: methyl 2-(1-hydroxy-2 -methylpropyl)thiazole-4-carboxylate (2), methyl 2-(1,2-dihydroxyethyl)thiazole-4-carboxylate (3), and methyl 7,7-dichloro-3-hydroxy-2-methyloctanoate (4). The absolute stereochemistry of 1 was determined by stereoselective syntheses of two degradation products 2 and 3 and two diastereomeric octanoates 7a,b (the dechloro derivatives of degradation product 4), and the enantioselective total synthesis of dolabellin itself. Dechlorodolabellin (23) was also synthesized.