12-methyldodecalactone | 69297-53-6

• 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: 12-methyldodecalactone
• 英文别名: 12-Me-DDL；13-methyl-oxacyclotridecan-2-one；Oxacyclotridecan-2-one, 13-methyl-
• CAS: 69297-53-6；88785-33-5；71736-24-8
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: FXQRCXMLOZUIDC-UHFFFAOYSA-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：

  12-methyldodecalactone 在 Candida antarctica lipase B 作用下， 以 甲苯 为溶剂， 以50%的产率得到(S)-12-methyldodecalactone
  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：

  2-methylenecyclododecanone 在 palladium on activated charcoal 氢气 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.0h， 生成 12-methyldodecalactone
  参考文献：
  名称：

  Preparation of macrocyclic lactones by ring closure of cesium carboxylates

  摘要：

  DOI：

  10.1021/ja00407a039

文献信息

• Chemical consequences of conformation in macrocyclic compounds
  作者：W.Clark Still、Igor Galynker

  DOI：10.1016/s0040-4020(01)93273-9

  日期：——

  In this paper we show that the conformational properties of medium- and large-ring organic molecules have profound consequences on the stereochemical course of their chemical reactions. Kinetic enolate alkylations, dimethylcuprate additions and catalytic hydrogenations were examined on a variety of monosubstituted 8- to 12-membered macrocyclic ketones and lactones, and the diastereomeric composition

  在本文中，我们表明中环和大环有机分子的构象性质对其化学反应的立体化学过程具有深远的影响。在各种单取代的8至12元大环酮和内酯上检查了动力学烯醇烷基化，二甲基cup酸酯的添加和催化氢化，并确定了产物的非对映异构体组成。在许多系统中，单个Me取代基提供了足够的构象偏差，可以高度立体选择性地形成新的不对称中心。
• Synthesen und Ringerweiterungsreaktionen von 2-(4-Hydroxyalkyl)-2-nitrocycloalkanonen
  作者：Hans Stach、Manfred Hesse

  DOI：10.1002/hlca.19860690715

  日期：1986.10.29

  Syntheses and Ring-Enlargement Reactions of 2-(4-Hydroxyalkyl)-2-nitrocycloalkanones

  2-（4-羟基烷基）-2-硝基环烷酮的合成和扩环反应
• 6,8,10-UNDECATRIEN-3-ONE OR 6,8,10-UNDECATRIEN-4-ONE, AND AROMA COMPOSITIONS
  申请人：Nakanishi Akira

  公开号：US20100137648A1

  公开（公告）日：2010-06-03

  This invention offers 6,8,10-undecatrien-3-one or 6,8,10-undecatrien-4-one which are represented by the following formula (1) [in the formula, either one of A and B stands for carbonyl group and the other stands for methylene group, and the wavy line signifies cis-form, trans-form, or a mixture of cis- and trans-form at an optional ratio] and which can reproduce an odor rich in naturality and freshness.

  该发明提供了由以下公式(1)表示的6,8,10-十一碳烯-3-酮或6,8,10-十一碳烯-4-酮[在公式中，A和B中的任意一个代表羰基，另一个代表亚甲基，波浪线表示顺式形式，反式形式或可选比例的顺反异构体混合物]，可以产生自然和清新的气味。
• 6,8,10-UNDECATRIEN-(3 OR 4)-ONE AND PERFUME COMPOSITION
  申请人：T. Hasegawa Co., Ltd.

  公开号：EP2168940B1

  公开（公告）日：2013-07-24
• 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