(S)-δ-dodecalactone | 108943-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-δ-dodecalactone
• 英文别名: (6S)-6-Heptyltetrahydro-2H-pyran-2-one；(6S)-6-heptyloxan-2-one
• CAS: 108943-47-1
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: QRPLZGZHJABGRS-NSHDSACASA-N

物化性质

• LogP：
  3.488 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  6
• 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

• 作为产物：
  描述：

  (S)-undec-1-en-4-ol 在 咪唑 、 正丁基锂 、 臭氧 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (S)-δ-dodecalactone
  参考文献：
  名称：

  Synthesis of Optically Active δ-Dodecalactone via Chiral Resolution Using CPF

  摘要：

  (通过(R)-3a-烯丙基-3,3a,4,5-四氢-2H-环戊并[b]呋喃（CPF）手性解析(±)-1-十一烯-4-醇，合成了(R)-6-庚基四氢吡喃-2-酮及其 S-对映体。R-enantiomer 具有浓郁的水果香味，而 S-enantiomer 的味道则柔和甜美，类似杏子的味道。

  DOI：

  10.1055/s-2007-985604

文献信息

• Highly Stereoselective 2-Oxonia-Cope Rearrangement: A Platform Enabling At-Will Control of Regio-, Enantio-, and Diastereoselectivity in the Vinylogous Aldol Reactions of Aldehydes
  作者：Akhil Padarti、Dongeun Kim、Hyunsoo Han

  DOI：10.1021/acs.orglett.7b03895

  日期：2018.2.2

  the vinylogous aldolation of aldehydes is described, which exploits 2-oxonia-Cope rearrangement reactions between two readily available partners, a set of rationally designed chiral homoallylic alcohol synthons and aldehydes, under simple conditions. In these processes, chirality transfer from the former to the latter is nearly perfect, giving rise to excellent enantio- and diastereoselectivity without

  描述了一种用于乙烯醇醛缩醛醛的截然不同的方法，其在简单条件下利用了两个容易获得的伙伴，一组合理设计的手性均烯丙基醇合成子和醛之间的2-氧代-Cope重排反应。在这些过程中，手性从前者向后者的转移几乎是完美的，从而产生了出色的对映异构和非对映异构选择性，而没有与传统的乙烯基醛醇缩合反应相关的区域选择性问题。
• Cascade Biotransformations via Enantioselective Reduction, Oxidation, and Hydrolysis: Preparation of (<i>R</i>)-δ-Lactones from 2-Alkylidenecyclopentanones
  作者：Ji Liu、Zhi Li

  DOI：10.1021/cs400101v

  日期：2013.5.3

  cascade biotransformation involving enantioselective reduction of a C═C double bond, Baeyer–Villiger oxidation, and lactone hydrolysis was developed as a green and sustainable tool for synthesizing enantiopure δ-lactones. One-pot cascade biotransformations were achieved with Acinetobacter sp. RS1 containing a novel enantioselective reductase and an enantioselective lactone hydrolase and Escherichia coli

  作为涉及绿色和可持续的合成对映纯δ-内酯的工具，首次涉及级联生物转化涉及C═C双键的对映选择性还原，Baeyer-Villiger氧化和内酯水解。不动杆菌属一锅级联生物转化。RS1含有新颖的对映选择性还原酶和对映体选择性内酯水解酶和大肠杆菌共表达的环己酮单加氧酶和葡糖脱氢酶，转换容易获得的2- alkylidenecyclopentanones 1 - 2成相应的有价值的香精香料（[R）-δ-内酯5 - 6在高ee中。一锅法合成优于报道的两步法制备。该概念对于开发其他包含C═C双键的底物的氧化还原级联反应很有用。
• Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the CC double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones
  作者：Ji Liu、Jinchuan Wu、Zhi Li

  DOI：10.1039/c4cc04150j

  日期：——

  Enoyl-ACP reductase (FabI) was identified as a non-OYE 'ene'-reductase for asymmetric reduction of the C=C double bond of alpha, beta-unsaturated ketones. Reduction of several 2-alkylidenecyclopentanones with A-FabI and E-FabI gave (R)-2-alkylcyclopentanones in 95-90% and 70-81% ee, respectively. The product ee was improved to 99-98% in high yield by subsequent one-pot biooxidation.

  烯丙基ACP还原酶（FabI）被鉴定为非OYE'烯'还原酶，用于不对称还原α，β-不饱和酮的C = C双键。用A-FabI和E-FabI还原几种2-亚烷基环戊酮，分别得到95-90％和70-81％ee的（R）-2-烷基环戊酮。通过随后的一锅式生物氧化，产物ee以高产率提高至99-98％。
• Proton‐Promoted Nickel‐Catalyzed Asymmetric Hydrogenation of Aliphatic Ketoacids
  作者：Chen‐Qiang Deng、Jiao Liu、Jia‐Hao Luo、Li‐Jin Gan、Jin Deng、Yao Fu

  DOI：10.1002/anie.202115983

  日期：2022.4.4

  A robust and efficient nickel–phosphine complex has been discovered for the asymmetric hydrogenation of aliphatic ketoacids. A proton promoted the activation of C=O bonds and controlled the stereoselectivity through hydrogen bonds to obtain the corresponding products in high yields with excellent enantioselectivities.

  已发现用于脂肪族酮酸的不对称氢化的稳健且有效的镍-膦配合物。质子促进了C=O键的活化，并通过氢键控制立体选择性，从而以高收率获得具有优异对映选择性的相应产物。
• Enantioselective Synthesis of <font>δ</font>-Lactones with Lipase-Catalyzed Resolution and Mitsunobu Reaction
  作者：Yasutaka Shimotori、Masakazu Aoyama、Tetsuo Miyakoshi

  DOI：10.1080/00397911.2010.529230

  日期：2012.3.1

  Both enantiomers of a series of delta-lactones (e.g., delta-decalactone, delta-dodelactone, and delta-hexadecalactone) were synthesized stereoselectively by Novozym 435-catalyzed resolution. Furthermore, only (S)-enantiomers of delta-lactones were synthesized with a combination of Novozym 435-catalyzed resolution and Mitsunobu reaction.