(2E,4S)-2,4-Dimethyl-2-decenal | 152899-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4S)-2,4-Dimethyl-2-decenal
• 英文别名: (2E,4S)-2,4-Dimethyldec-2-enal；(E,4S)-2,4-dimethyldec-2-enal
• CAS: 152899-18-8
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: LVAYNJXCBOHXPD-UTEVDWOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,4S)-2,4-Dimethyl-2-decenal 在 lithium hydroxide 、 柠檬酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 4.25h， 生成 (2E,4E,6S)-N-[(3S)-2,8-dioxo-1-oxaspiro[4.5]deca-6,9-dien-3-yl]-4,6-dimethyldodeca-2,4-dienamide
  参考文献：
  名称：

  直接合成阿拉伯糖蛋白的研究

  摘要：

  描述了导致环己酮双环氧乙烷构建为aranorosin中存在的1-氧杂螺并[4,5]癸烷部分的方法。

  DOI：

  10.1016/0040-4039(91)80236-y
• 作为产物：
  描述：

  (2E,4S)-2,4-Dimethyl-2-decen-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到(2E,4S)-2,4-Dimethyl-2-decenal
  参考文献：
  名称：

  二环氧环己酮抗生素阿诺罗星和新型合成类似物的全合成

  摘要：

  描述了手性形式的新型抗生素阿糖胞苷的简短合成，其在关键步骤中采用了（i）酪氨酸衍生物的新型高价碘介导的氧化羟基化作用和（ii）立体控制的顺式-双环氧化。采用相似的方法制备6'-表皮阿糖胞苷，从而建立天然化合物的立体化学，并制备新的阿糖胞苷类似物。描述了一种有机金属路线，该路线产生了脱酰胺基芳族松香。

  DOI：

  10.1039/p19960001385

文献信息

• A concise synthesis of the novel antibiotic aranorosin
  作者：Alexander McKillop、Lee McLaren、Robert J. Watson、Richard J.K. Taylor、Norman Lewis

  DOI：10.1016/s0040-4039(00)73870-6

  日期：1993.8

  A short synthesis of the novel antibiotic aranorosin is described which employs a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative in the key step. A similar procedure was employed to prepare 6′-epiaranorosin, and hence establish the stereochemistry of the natural compound.

  描述了新型抗生素阿糖胞苷的简短合成，其在关键步骤中采用了新的高价碘介导的酪氨酸衍生物的氧化羟基化作用。采用类似的方法制备6'-表皮阿拉伯糖球蛋白，因此建立了天然化合物的立体化学。
• Total synthesis and structure assignment of the antitumor antibiotic aranorosin
  作者：Peter Wipf、Yuntae Kim、Paul C. Fritch

  DOI：10.1021/jo00077a050

  日期：1993.12

  The structurally unique antifungal and antitumor antibiotic aranorosin was prepared in a convergent, stereoselective sequence. Oxidative cyclization of N-protected L-tyrosine, followed by face-selective 1,2-addition of [(benzyloxy)methyl]lithium, Henbest oxidation in the presence of Kishi's radical inhibitor, and simultaneous N,O-deprotection led to an amino diol which was N-acylated with the fatty acid side-chain segment. After a low-temperature reduction of the lactone moiety to the lactol, the carbonyl function was regenerated under neutral conditions by diol cleavage with sodium periodate. Preparation of the acid side chain involved a diastereoselective imide alpha-alkylation directed by Evans' oxazolidinone auxiliary, followed by a series of Wittig-Horner chain extensions. Since the relative configuration at the C (6') position of the natural product had not been determined, we prepared both the (6'S) and the (6'R) isomers of aranorosin. Comparison of synthetic material with the reported spectral data for natural (-)-aranorosin, especially H-1 and C-13 NMR and [alpha]D, did not allow a definitive assignment. After purification of a sample of the isolated material from Pseudoarachniotus roseus, the corrected [alpha]D strongly indicated the (6'R)-stereochemistry for the natural compound. This assignment was confirmed by circular dichroism spectra for (6'S)- and (6'R)-aranorosin and the natural material.