(S)-7-methyl-1,5-diazacyclotetradecane

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-7-methyl-1,5-diazacyclotetradecane
• 英文别名: (S)-(-)-haliclorensin；(S)-haliclorensin；haliclorensin；(7S)-7-methyl-1,5-diazacyclotetradecane
• 化学式: C₁₃H₂₈N₂
• 分子量: 212.379
• InChiKey: OFPMSWKVQNUTSL-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  戊二醛 在 platinum(IV) oxide 、 palladium on activated charcoal T406石油添加剂 、 sodium tetrahydroborate 、 正丁基锂 、 氯化亚砜 、 甲基叔丁基醚 、 硫酸 、 氢气 、 碘 、 甲烷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 353.25h， 生成 (S)-7-methyl-1,5-diazacyclotetradecane
  参考文献：
  名称：

  Enantiodivergent Synthesis of Both Enantiomers of Marine Alkaloids Haliclorensin and Isohaliclorensin, a Constituent of Halitulin

  摘要：

  Starting from (3R)-5-benzotriazolyl-3-phenylperhydropyrido[2,1-b][1,3]oxazole 9, the enantiodivergent syntheses of both enantiomers of the marine alkaloids haliclorensin 1 and isohaliclorensin 3 have been achieved. Our syntheses feature ring-expansion reactions for the formation of the aza-macrocycle ring system of 3 and sequential ring-expansion reactions (aza-Claisen rearrangement and Zip reaction) for the formation of the aza-macrocycle ring system of 1.

  DOI：

  10.1021/ol049887k

文献信息

• Access to Enantiopure 4-Substituted 1,5-Aminoalcohols from Phenylglycinol-Derived δ-Lactams: Synthesis of <i>Haliclona</i> Alkaloids
  作者：Mercedes Amat、Guillaume Guignard、Núria Llor、Joan Bosch

  DOI：10.1021/jo5002627

  日期：2014.3.21

  LiNH2BH3-promoted reductive opening of 8-substituted phenylglycinol-derived oxazolopiperidone lactams leads to enantiopure 4-substituted-5-aminopentanols, which are used as starting building blocks in the synthesis of the Haliclona alkaloids haliclorensin C, haliclorensin, and halitulin (formal). The starting lactams are easily accessible by a cyclocondensation reaction of (R)-phenylglycinol with racemic γ-subtituted

  LiNH 2 BH 3促进的8取代的苯基甘氨醇衍生的恶唑并哌啶酮内酰胺的还原性打开反应导致对映体纯的4取代的5-氨基戊醇，这些化合物被用作Haliclona生物碱类盐蒜素C，盐蒜素和Hallitulin（正式的）。起始内酰胺很容易通过（R）-苯基甘氨醇与外消旋的γ-取代的δ-氧代酯的环缩合反应获得，该过程涉及动态动力学拆分。
• Revision of the structure of haliclorensin to (S)-7-methyl-1,5-diazacyclotetradecane and confirmation of the new structure by synthesis
  作者：Markus R Heinrich、Yoel Kashman、Peter Spiteller、Wolfgang Steglich

  DOI：10.1016/s0040-4020(01)01020-1

  日期：2001.12

  A reinvestigation of the marine alkaloid haliclorensin led to a revision of the proposed structure to 7-methyl-1,5-diazacyclotetradecane. The new structure was confirmed by total synthesis of both optical forms. According to chiroptical measurements and GC–MS investigations, natural haliclorensin consists of a 3:1 mixture of the (S)- and (R)-enantiomers.

  对海洋生物碱盐蒜素的重新研究导致将拟议结构改制成7-甲基-1,5-二氮杂环十四烷。通过两种光学形式的全合成证实了新结构。根据手足术测量和GC-MS研究，天然水杨素由3：1的（S）-和（R）-对映体混合物组成。
• Enantiodivergent Synthesis of Both Enantiomers of Marine Alkaloids Haliclorensin and Isohaliclorensin, a Constituent of Halitulin
  作者：Jian-Feng Zheng、Li-Ren Jin、Pei-Qiang Huang

  DOI：10.1021/ol049887k

  日期：2004.4.1

  Starting from (3R)-5-benzotriazolyl-3-phenylperhydropyrido[2,1-b][1,3]oxazole 9, the enantiodivergent syntheses of both enantiomers of the marine alkaloids haliclorensin 1 and isohaliclorensin 3 have been achieved. Our syntheses feature ring-expansion reactions for the formation of the aza-macrocycle ring system of 3 and sequential ring-expansion reactions (aza-Claisen rearrangement and Zip reaction) for the formation of the aza-macrocycle ring system of 1.