(2R,4E,6E,8S)-2,4,8-trimethyl-4,6-decadienal | 359766-17-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4E,6E,8S)-2,4,8-trimethyl-4,6-decadienal
• 英文别名: (2R,4E,6E,8S)-2,4,8-trimethyldeca-4,6-dienal
• CAS: 359766-17-9
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: LDZJXCOAVDNXGB-XSXWTYNNSA-N

物化性质

• 沸点：
  273.4±9.0 °C(Predicted)
• 密度：
  0.851±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (2R,4E,6E,8S)-2,4,8-trimethyl-4,6-decadienal 在 4-二甲氨基吡啶 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 二氯甲烷 为溶剂， 反应 51.25h， 生成 Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester
  参考文献：
  名称：

  Total Synthesis of Nafuredin, a Selective NADH-fumarate Reductase Inhibitor

  摘要：

  Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach. The C1-C8 and C9-C18 segments were derived efficiently from D-glucose and (S)-(-)-2-methyl-1-butanol, respectively, coupled by stereoselective Julia olefination, and converted to nafuredin.

  DOI：

  10.1021/ol010089t
• 作为产物：
  描述：

  (R)-4-Benzyl-3-((4E,6E)-(2R,8S)-2,4,8-trimethyl-deca-4,6-dienoyl)-oxazolidin-2-one 在 锂硼氢 、 乙醇 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 (2R,4E,6E,8S)-2,4,8-trimethyl-4,6-decadienal
  参考文献：
  名称：

  Total Synthesis of Nafuredin, a Selective NADH-fumarate Reductase Inhibitor

  摘要：

  Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach. The C1-C8 and C9-C18 segments were derived efficiently from D-glucose and (S)-(-)-2-methyl-1-butanol, respectively, coupled by stereoselective Julia olefination, and converted to nafuredin.

  DOI：

  10.1021/ol010089t

文献信息

• 1,4-Pentenyne as a Five-Carbon Synthon for Efficient and Selective Syntheses of Natural Products Containing 2,4-Dimethyl-1-penten-1,5-ylidene and Related Moieties by Means of Zr-Catalyzed Carboalumination of Alkynes and Alkenes
  作者：Gangguo Zhu、Ei-ichi Negishi

  DOI：10.1002/chem.200701512

  日期：2008.1

  Two highly efficient protocols for enantioselective synthesis of 2,4-dimethyl-1-penten-1,5-ylidene derivatives involve the combined use of the Zr-catalyzed methylalumination of alkynes (ZMA) and the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA). The ZMA/ZACA protocol has been applied to the synthesis of a nafuredin intermediate 14 and a potential intermediate 18 for milbemycin beta 3,

  对映选择性合成2,4-二甲基-1-戊烯-1,5-亚烷基衍生物的两个高效方案涉及Zr催化的炔烃甲基铝化（ZMA）和Zr催化的烯烃不对称碳铝化（ZACA）的组合使用）。ZMA / ZACA协议已被用于合成那富瑞丁中间体14和米尔贝霉素beta 3的潜在中间体18，而ZACA / ZMA协议已被应用于合成（-）-bafilomycin A（1）中间体25岁
• Design, synthesis, and biological evaluation of air-stable nafuredin-γ analogs as complex I inhibitors
  作者：Masaki Ohtawa、Mari Matsunaga、Keiko Fukunaga、Risa Shimizu、Eri Shimizu、Shiho Arima、Junko Ohmori、Kiyoshi Kita、Kazuro Shiomi、Satoshi Omura、Tohru Nagamitsu

  DOI：10.1016/j.bmc.2015.01.030

  日期：2015.3

  Nafuredin-gamma (2), converted from nafuredin (1) under mild basic conditions, demonstrates potent and selective inhibitory activity against helminth complex I. However, 2 is unstable in air because the conjugated dienes are oxygen-labile. To address this, we designed and synthesized air-stable nafuredin-gamma analogs. Although the complex I inhibitory activities of all the new nafuredin-gamma analogs were lower than that of 2, all were in the high nM range (IC50: 300-820 nM). (C) 2015 Elsevier Ltd. All rights reserved.
• Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase
  作者：Tohru Nagamitsu、Daisuke Takano、Kazuro Shiomi、Hideaki Ui、Yuichi Yamaguchi、Rokuro Masuma、Yoshihiro Harigaya、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1016/s0040-4039(03)01583-1

  日期：2003.8

  Nafuredin-gamma (2) converted from nafuredin (1) under mild basic conditions showed the same inhibitory activity and selectivity against NADH-fumarate reductase as 1. Total synthesis of 2, a proposed active form of 1, has been accomplished by a convergent approach using Stille coupling. (C) 2003 Elsevier Ltd. All rights reserved.
• Total Synthesis of Nafuredin, a Selective NADH-fumarate Reductase Inhibitor
  作者：Daisuke Takano、Tohru Nagamitsu、Hideaki Ui、Kazuro Shiomi、Yuuichi Yamaguchi、Rokuro Masuma、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1021/ol010089t

  日期：2001.7.1

  Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach. The C1-C8 and C9-C18 segments were derived efficiently from D-glucose and (S)-(-)-2-methyl-1-butanol, respectively, coupled by stereoselective Julia olefination, and converted to nafuredin.