(R)-δ-decalactone | 2825-91-4

• 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: (R)-δ-decalactone
• 英文别名: (R)-(+)-tetrahydro-6-pentyl-2H-pyran-2-one；(R)-6-pentyltetrahydro-2H-pyran-2-one；(6R)-6-pentyltetrahydro-2H-pyran-2-one；(R)-6-Pentyltetrahydropyran-2-one；(6R)-6-pentyloxan-2-one
• CAS: 2825-91-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: GHBSPIPJMLAMEP-SECBINFHSA-N

物化性质

• 沸点：
  267.2±8.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)
• LogP：
  2.417 (est)
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  存储于阴凉干燥处。

反应信息

• 作为反应物：
  描述：

  (R)-δ-decalactone 在 四乙基氢氧化铵 作用下， 生成
  参考文献：
  名称：

  Enantiomeric separation of carboxylic acids having chiral centers remote from the carboxyl group by labelling with a chiral fluorescent derivatization reagent

  摘要：

  Enantiomeric separations of 2-, 3-, 4-, 5- and 6-methyl fatty acids and 3-, 4- and 5-hydroxy fatty acids derivatized with (S)-(+)-2-(anthracene-2,3-dicarboximido)-1-propyl trifluoromethanesulfonate are described. Although there are 4-8 bond distances between the chiral centers of these diastereomeric derivatives, they are separated on HPLC and detected at fmol levels. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01616-x
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 硫酸氢铵 、 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 L-丙氨酸 、 magnesium sulfate 、 calcium chloride 、 蔗糖 、 β-乳糖 作用下， 以 水 为溶剂， 生成 (R)-δ-decalactone
  参考文献：
  名称：

  Studies on the biosynthesis of aliphatic lactones in Sporobolomyces odorus. Conversion of (S)- and (R,S)-13-hydroxy-(Z,E)-9,11-octadecadienoic acid into optically pure (R)-.delta.-decalactone

  摘要：

  The mechanism of the biotransformations of (S)- and (R,S)-13-hydroxy-(Z,E)-9,11-octadecadienoic acid, 1, into optically pure (R)-delta-decalactone, 12, catalyzed by the yeast Sporobolomyces odorus, was studied, and an oxidation of the secondary hydroxy group followed by an enantioselective reduction of the keto acid intermediate was found to be responsible for the stereochemical outcome.

  DOI：

  10.1021/jo00033a007

文献信息

• Simple Preparation of<i>Rhodococcus erythropolis</i>DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones
  作者：Enriqueta Martinez-Rojas、Teresa Olejniczak、Konrad Neumann、Leif-Alexander Garbe、Filip Boratyñski

  DOI：10.1002/chir.22623

  日期：2016.9

  In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane‐1,4‐diol (2a) and decane‐1,5‐diol (3a) into the corresponding γ‐ (2b) and δ‐decalactones (3b) with yield of 80% and enantiomeric excess (ee) = 75% and ee = 90%, respectively. Among oxidation of meso diols, (−)‐(1S,5R)‐cis‐3‐oxabicyclo[4

  在当前的研究中，我们提出了一个绿色的工具箱来生产生态化合物，如内酯部分。红球菌DSM 44534细胞已用于将癸烷-1,4-二醇（2a）和癸烷-1,5-二醇（3a）氧化成相应的γ-（2b）和δ-癸内酯（3b） 80％和对映体过量（ee）= 75％，ee = 90％。在内消旋二醇的氧化中，（-）-（1S，5R）-顺式-3-氧杂双环[4.3.0] non-7-en-2-1（5a）的产率为56％，ee = 76％，以及（ - ） - （2R，3S） -顺式-内切形成了100％收率且ee = 90％的-3-oxabicyclocyclo [2.2.1] dec-7-en-2-one（6a）。值得一提的是R.红球菌DSM 44534在含有乙醇作为能源和碳的唯一来源矿物培养基中生长手性28：623-627，2016。©2016 Wiley Periodicals，Inc.
• Efficient Stereoselective Synthesis of Structurally Diverse γ‐ and δ‐Lactones Using an Engineered Carbonyl Reductase
  作者：Meng Chen、Xiao‐Yan Zhang、Chen‐Guang Xing、Chao Zhang、Yu‐Cong Zheng、Jiang Pan、Jian‐He Xu、Yun‐Peng Bai

  DOI：10.1002/cctc.201900382

  日期：2019.6.6

  efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500‐fold) and thermostability toward 14 γ‐/δ‐keto acids and esters, compared with the wild‐type enzyme, with 110‐fold enhancement in catalytic efficiency (kcat/Km) toward methyl 4‐oxodecanoate. The preparative synthesis of alkyl and aromatic γ‐ and δ‐lactones

  结构结构多样的γ-和δ-内酯是利用粘质沙雷氏菌（Sm CR V4）中的一种工程化羰基还原酶有效地立体选择性合成的。与野生型酶相比，Sm CR V4表现出更高的活性（最高达500倍）和对14种γ-/δ-酮酸和酯的热稳定性，催化效率提高了110倍（k cat / K m）对4-氧代十二烷甲酸甲酯。证明了烷基和芳香族γ-和δ-内酯的制备合成，其ee率为95％-> 99％，收率为78％-90％。最高时空产量为1175 g L -1  d -1，达到了（R）-γ-癸内酯
• Stereoselective synthesis of chiral δ-lactones <i>via</i> an engineered carbonyl reductase
  作者：Tao Wang、Xiao-Yan Zhang、Yu-Cong Zheng、Yun-Peng Bai

  DOI：10.1039/d1cc04542c

  日期：——

  A carbonyl reductase variant, SmCRM5, from Serratia marcescens was obtained through structure-guided directed evolution. The variant showed improved specific activity (U mg−1) towards most of the 16 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of 13 γ-/δ-lactones. In particular, SmCRM5 showed a 13.8-fold higher specific activity towards the model substrate

  来自粘质沙雷氏菌的羰基还原酶变体Sm CR M5是通过结构引导的定向进化获得的。该变体对 16 种测试底物中的大多数表现出改善的比活性 (U mg -1 )，并在 13 种 γ-/δ-内酯的不对称合成中提供高达 99% 的高立体选择性。特别是，SmCR M5对模型底物（即5-氧代癸酸）的比活性高出 13.8 倍，并在 99% ee 中产生 ( R )-δ-癸内酯，时空产率 (STY) 为 301 g L -1 d -1. 六种δ-内酯的高收率和高对映体纯度的制备表明这些高附加值化学品的生物催化合成是可行的，为贵金属催化提供了一种具有成本效益的绿色替代品。
• (S)-5-hydroxydecanoic acid and its therapeutic composition
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0410446A1

  公开（公告）日：1991-01-30

  The present invention relates to a compound selected from the group consisting of (S)-5-­hydroxydecanoic acid, a salt, a solvate and a solvate of said salt thereof and relates to methods for producing the compound, comprising of inversion of the configuration and also relates to a pharmaceutical composition for treatment of cardiovascular diseases such as arrhythmia and ischemic heart diseases, or diabates.

  本发明涉及一种选择自(S)-5-羟基癸酸、盐、溶剂和该盐的溶剂的组合物的化合物，并涉及用于生产该化合物的方法，包括构象的倒转，并涉及一种用于治疗心血管疾病如心律失常和缺血性心脏病或糖尿病的药物组合物。
• A facile approach towards synthesis of verbalactone and biologically active δ-lactones using d-glucose
  作者：Ashish Garg、Vinod K. Singh

  DOI：10.1016/j.tet.2009.08.054

  日期：2009.10

  A general synthetic approach has been developed for the asymmetric synthesis of chiral δ-lactones and verbalactone using d-glucose. The key intermediate used in this approach was α-diazoketone.

  已经开发了用于使用d-葡萄糖不对称合成手性δ-内酯和韦拉内酯的通用合成方法。该方法中使用的关键中间体是α-二氮杂酮。