(S)-12-methyldodecalactone | 206124-08-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (S)-12-methyldodecalactone
• 英文别名: (S)-12-Me-DDL；(13S)-13-methyl-oxacyclotridecan-2-one
• CAS: 206124-08-5
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: FXQRCXMLOZUIDC-LBPRGKRZSA-N

物化性质

• 沸点：
  312.2±10.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-12-methyldodecalactone 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 (R)-(12-azidotridecyloxy)triphenylmethane
  参考文献：
  名称：

  CAL-B catalyzed synthesis of chiral polyamides

  摘要：

  CAL-B (Novozym 435) plays a dual role in our approach to chiral polyamides. It is used to introduce the appropriate chirality in the synthesis of monomers (amino-esters and diamines) from racemic 12-methyldodecalactone and then to catalyze their polycondensation. The AB and AABB enzymatic polymerizations have been carried out under reduced pressure; they give rise to optically active polymers in good yield, with a good degree of polymerization, and a narrow polydispersity index. This approach demonstrates that the presence of a methyl group at the stereogenic center at the alpha-position relative to the nitrogen atom does not slow down the polymerization as compared with the polycondensation of a related achiral monomer. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.021
• 作为产物：
  描述：

  (2S)-1-[2-(8-bromooctyl)-1,3-dithian-2-yl]propan-2-ol 在 W-2 Raney Ni 氢氧化钾 、 silver perchlorate 、 三苯基膦 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 生成 (S)-12-methyldodecalactone
  参考文献：
  名称：

  Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones

  摘要：

  Both enantiomers of macrocyclic lactones, 12-tridecanolide (1), 13-tetradecanolide (2), 14-pentadecanolide (3) and 15-hexadecanolide (4), were synthesized utilizing (S)-(-)-beta-hydroxythioacetal (5) as the chiral building block. Key steps are the C-alkylation of a dianion derived from 5 with alkyl dibromides followed by conversion of functional groups and the two macrolactonization. The both enantiomers of 1 similar to 4 have been obtained by reductive desulfurization of the dithiane moiety.

  DOI：

  10.3987/com-97-7991

文献信息

• An asymmetric synthesis of acyclic and macrocyclic .alpha.-alkyl ketones. The role of (e)- and (z)-lithioenamines
  作者：A. I. Meyers、Donald R. Williams、Steven White、Gary W. Erickson

  DOI：10.1021/ja00401a029

  日期：1981.6
• Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones
  作者：Yoshihiro Noda、Hitoshi Kashin

  DOI：10.3987/com-97-7991

  日期：——

  Both enantiomers of macrocyclic lactones, 12-tridecanolide (1), 13-tetradecanolide (2), 14-pentadecanolide (3) and 15-hexadecanolide (4), were synthesized utilizing (S)-(-)-beta-hydroxythioacetal (5) as the chiral building block. Key steps are the C-alkylation of a dianion derived from 5 with alkyl dibromides followed by conversion of functional groups and the two macrolactonization. The both enantiomers of 1 similar to 4 have been obtained by reductive desulfurization of the dithiane moiety.
• CAL-B catalyzed synthesis of chiral polyamides
  作者：Florent Poulhès、Dominique Mouysset、Gérard Gil、Michèle P. Bertrand、Stéphane Gastaldi

  DOI：10.1016/j.tetasy.2012.05.021

  日期：2012.6

  CAL-B (Novozym 435) plays a dual role in our approach to chiral polyamides. It is used to introduce the appropriate chirality in the synthesis of monomers (amino-esters and diamines) from racemic 12-methyldodecalactone and then to catalyze their polycondensation. The AB and AABB enzymatic polymerizations have been carried out under reduced pressure; they give rise to optically active polymers in good yield, with a good degree of polymerization, and a narrow polydispersity index. This approach demonstrates that the presence of a methyl group at the stereogenic center at the alpha-position relative to the nitrogen atom does not slow down the polymerization as compared with the polycondensation of a related achiral monomer. (c) 2012 Elsevier Ltd. All rights reserved.