(3S,8E)-1,3-二羟基-8-癸烯-5-酮 | 86918-62-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (3S,8E)-1,3-二羟基-8-癸烯-5-酮
• 英文名称: streptenol A
• 英文别名: (S)-(+)-streptenol A；1,3-Dihydroxy-8-decen-5-one；(E,3S)-1,3-dihydroxydec-8-en-5-one
• CAS: 86918-62-9
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: SHHVNLZCXWAKNG-PBKGFPTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  (3S,8E)-1,3-二羟基-8-癸烯-5-酮 在 lithium aluminium tetrahydride 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 37.0h， 生成 (-)-(3R,5R,8E)-methanesulfonic acid 5-[(methylsulfonyl)amino]-3-[(methylsulfonyl)oxy]dec-8-enyl ester
  参考文献：
  名称：

  Synthesis of (+)-(S)-Streptenol A and Biomimetic Synthesis of (2R,4S)- and (2S,4S)-2-(Pent-3-enyl)piperidin-4-ol

  摘要：

  (+)-(S)-Streptenol A 是通过将 1,3-二硫杂烯与光学纯的环氧化物偶联来合成的。因此，(+)-(S)-streptenol A 的绝对构型与 (S)-苹果酸的构型相关联。从 streptenol A 出发，可以方便地制备出一个肟，并通过对其立体选择性地还原，得到了 (3S,5R)-和 (3S,5S)-氨基streptenol。经过环化后，进一步获得了构型纯的 2,4-官能化哌啶生物碱。

  DOI：

  10.1002/(sici)1522-2675(19990707)82:7<1111::aid-hlca1111>3.0.co;2-l
• 作为产物：
  描述：

  (4E)-4-己烯醛 在 正丁基锂 、 mercury(II) perchlorate 、 4 A molecular sieve 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 168028.58h， 生成 (3S,8E)-1,3-二羟基-8-癸烯-5-酮
  参考文献：
  名称：

  Synthesis of (+)-(S)-Streptenol A and Biomimetic Synthesis of (2R,4S)- and (2S,4S)-2-(Pent-3-enyl)piperidin-4-ol

  摘要：

  (+)-(S)-Streptenol A 是通过将 1,3-二硫杂烯与光学纯的环氧化物偶联来合成的。因此，(+)-(S)-streptenol A 的绝对构型与 (S)-苹果酸的构型相关联。从 streptenol A 出发，可以方便地制备出一个肟，并通过对其立体选择性地还原，得到了 (3S,5R)-和 (3S,5S)-氨基streptenol。经过环化后，进一步获得了构型纯的 2,4-官能化哌啶生物碱。

  DOI：

  10.1002/(sici)1522-2675(19990707)82:7<1111::aid-hlca1111>3.0.co;2-l

文献信息

• Asymmetric Synthesis of (+)- and (–)-Streptenol A
  作者：Dieter Enders、Thomas Hundertmark

  DOI：10.1002/(sici)1099-0690(199904)1999:4<751::aid-ejoc751>3.0.co;2-r

  日期：1999.4

  The asymmetric synthesis of (+)-streptenol A was carried out in ten steps and with high enantioselectivity (ee ≥ 96%). The key steps are the α-alkylation of 2,2-dimethyl-1,3-dioxan-5-one RAMP hydrazone A (1), subsequent deoxygenation and elaboration of the side chain via aldehyde B to furnish (+)-streptenol A in 23% overall yield. In analogy, the enantiomer (–)-streptenol A was synthesized using the

  (+)-链烯醇 A 的不对称合成分十步进行，具有高对映选择性（ee ≥ 96%）。关键步骤是 2,2-二甲基-1,3-二恶烷-5-one RAMP 腙 A (1) 的 α-烷基化，随后通过醛 B 脱氧和加工侧链以提供 (+)-链烯醇 A总产率为 23%。类似地，使用相应的 SAMP 腙以 18% 的总产率合成对映异构体 (-)-链烯醇 A。
• Chiral building blocks from streptomyces-2.1 stereoselective transformation of streptenol a into 3-methyl-δ-lactones
  作者：Joachim Adam、Robert Klein、Susanne Grabley、Peter Hammann

  DOI：10.1016/0040-4020(95)00438-e

  日期：1995.7

  The stereoselective synthesis of both enantiomeric forms of 3-alkyl-streptenols A 7-9 and ent-7-9 in four steps is described. Hereby, the stereoselective acetalization to the pyrans 2a and 2b directed by the solvent and the catalyst used was a key step in the reaction sequence. The 3-alkyl-streptenols represents interesting chiral building blocks which can be used for the synthesis of analogues of HMG-CoA inhibitors, e.g. 3-methyl-delta-lactones.
• Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons
  作者：De Run Li、Andiappan Murugan、J. R. Falck

  DOI：10.1021/ja076802c

  日期：2008.1.1

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
• Secondary metabolites by chemical screening -13. Enantioselective synthesis of δ-lactones from streptenola, achiral building block from streptomyces
  作者：Yvonne Romeyke、Martin Keller、Heinz Kluge、Susanne Grabley、Peter Hammann

  DOI：10.1016/s0040-4020(01)86398-5

  日期：1991.1

  The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enantiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described. The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group. This reaction furnishes in one step the sigma-lactones 3a and 3b and requires no protecting group.
• Synthesis of (+)-(S)-Streptenol A and Biomimetic Synthesis of (2R,4S)- and (2S,4S)-2-(Pent-3-enyl)piperidin-4-ol
  作者：Heribert Dollt、Peter Hammann、Siegfried Blechert

  DOI：10.1002/(sici)1522-2675(19990707)82:7<1111::aid-hlca1111>3.0.co;2-l

  日期：1999.7.7

  (+)-(S)-Streptenol A is synthesized by coupling a 1,3-dithiane with an optically pure epoxide. The absolute configuration of (+)-(S)-streptenol A is thereby correlated with that of (S)-malic acid. Stereoselective reduction of an oxime that could easily be prepared from streptenol A gave the (3S,5R)- and (3S,5S)-aminostreptenols, and after cyclization, configurationally pure 2,4-functionalized piperidine alkaloids.

  (+)-(S)-Streptenol A 是通过将 1,3-二硫杂烯与光学纯的环氧化物偶联来合成的。因此，(+)-(S)-streptenol A 的绝对构型与 (S)-苹果酸的构型相关联。从 streptenol A 出发，可以方便地制备出一个肟，并通过对其立体选择性地还原，得到了 (3S,5R)-和 (3S,5S)-氨基streptenol。经过环化后，进一步获得了构型纯的 2,4-官能化哌啶生物碱。