(5S)-isopropyl-2-methylcyclopent-1-enecarboxaldehyde | 62994-35-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5S)-isopropyl-2-methylcyclopent-1-enecarboxaldehyde
• 英文别名: (3S)-irid-1-en-7-al；(3S)-1-iriden-7-al；(-)-1-Methyl-2-formyl-3-isopropylcyclopenten；1-Cyclopentene-1-carboxaldehyde, 2-methyl-5-(1-methylethyl)-, (S)-；(5S)-2-methyl-5-propan-2-ylcyclopentene-1-carbaldehyde
• CAS: 62994-35-8
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: NDYPMNCLXBBUQQ-VIFPVBQESA-N

物化性质

• 沸点：
  216.8±19.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (5S)-isopropyl-2-methylcyclopent-1-enecarboxaldehyde 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.33h， 生成 (3S)-1-iriden-7-ol
  参考文献：
  名称：

  Srikrishna; Nagaraju, Gopalasetty, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 1, p. 73 - 76

  摘要：

  DOI：
• 作为产物：
  描述：

  甜橙提取物 在 platinum(IV) oxide 、 sodium periodate 、 过甲酸 、 氢气 、 L-脯氨酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 (5S)-isopropyl-2-methylcyclopent-1-enecarboxaldehyde
  参考文献：
  名称：

  通过催化有效的两步法合成多聚酰胺

  摘要：

  Puleganic酰胺显示出有趣的驱蚊特性。已开发出一种新的合成这种酰胺的方法，该方法涉及一锅方案中的有机催化环化反应和金属催化的氢化反应。生态友好的氧化胺化仅需一个纯化步骤，即可为斑节胺提供可接受的收率。

  DOI：

  10.1016/j.tetlet.2018.06.067

文献信息

• A route, via tetraquinane, to the 5-8-5 carbocyclic nucleus of fusicoccins and ophiobolins
  作者：Goverdhan Mehta、Nacharaju Krishnamurthy

  DOI：10.1039/c39860001319

  日期：——

  Short, stereoselective syntheses of dicyclopenta[a,d]cyclo-octane-based diones (14) and (+)-(22)via a 5-5-5-5→5-8-5 strategy are reported; our approach constitutes an effective methodology for constructing fusicoccane and ophiobolane-type natural products.

  报道了通过5-5-5-5→5-8-5策略的基于二环戊基[ a，d ]环辛烷的二酮（14）和（+）-（22）的短的，立体选择性的合成。我们的方法构成了构建呋喃西林和ophiobolane型天然产物的有效方法。
• Synthetic Photochemistry. XXXIV. Synthetic Strategy of 5-8-5-Membered Tricyclic Higher Terpenoids Based on the Condensation of Two Optically-Active Iridoids, C₁₀-Synthons Obtained from Photo-Cycloadduct of Methyl 2,4-Dioxopentanoate–Isoprene, and Its Application to a Synthesis of the Basic Carbon Skeleton of Fusicoccane
  作者：Nobuo Kato、Kohji Nakanishi、Hitoshi Takeshita

  DOI：10.1246/bcsj.59.1109

  日期：1986.4

  One of the photocycloadducts obtained during methyl 2,4-dioxopentanoate to isoprene was converted to optically active iridoids. Using a CrCl2 reductive-coupling reaction, proper combinations of two kinds of enantiomeric iridoids, 1-iriden-7-al and 9-benzyloxy-7-chloro-1-iridene, produced versatile intermediates for various types of 5-8-5-membered tricyclic natural products. From one such product, fusicocca-2,8,10(14)-triene (1) was synthesized by sequential transformations.

  2,4-二氧代戊酸甲酯生成异戊二烯过程中获得的光环加合物之一被转化为光学活性环烯醚萜。利用CrCl2还原偶联反应，将两种对映体环烯醚萜化合物1-iriden-7-al和9-benzyloxy-7-氯-1-iridene适当组合，产生了各种类型5-8-5-的多功能中间体。元三环天然产物。通过连续转化，从这样的一种产物中合成了 fusicocca-2,8,10(14)-triene (1)。
• SYNTHESIS OF FUSICOCCA-2,8,10-TRIENE, A BIOGENETIC MISSING LINK, STARTING FROM STEREOSPECIFIC CONDENSATION OF TWO IRIDOID SYNTHONS
  作者：Hitoshi Takeshita、Nobuo Kato、Kohji Nakanishi、Hirotaka Tagoshi、Toshihide Hatsui

  DOI：10.1246/cl.1984.1495

  日期：1984.9.5

  From two units of iridoid C10-synthons which could be prepared from one of the photoadducts of isoprene and methyl 2,4-dioxopentanoate, the hydrocarbon which can be designated as fusicocca-2,8,10-triene, a missing link in the biogenesis, was stereospecifally synthesized.

  来自两个单元的环烯醚萜 C10-合成子，可以从异戊二烯和 2,4-二氧代戊酸甲酯的光加合物之一制备，碳氢化合物可以被指定为 fusicocca-2,8,10-triene，生物发生中的一个缺失环节, 是立体特异性合成的。
• Synthetic Photochemistry. XLII. Total Synthesis of Cycloaraneosene, a Fundamental Hydrocarbon of 5–8–5-Membered Tricydic Diterpenoid from<i>Sordaria araneosa</i>
  作者：Nobuo Kato、Shinya Tanaka、Hitoshi Takeshita

  DOI：10.1246/bcsj.61.3231

  日期：1988.9

  A 5–8–5-membered tricyclic diterpene, cycloaraneosene, has been totally synthesized via a stereoselective condensation of two units of optically active iridoids, a Cope rearrangement, a chemical reduction of the tetrasubstituted double bond, and the formation of an eight-membered ring. The proposed structure of natural hydroxycycloaraneosene should be revised to 8β-hydroxycycloaraneosene, judging from the NMR spectral data.

  通过立体选择性缩合两个单元的光学活性虹彩、科普重排、四取代双键的化学还原以及八元环的形成，完全合成了一种 5-8-5 元三环二萜--环胂烯。从核磁共振光谱数据来看，拟议的天然羟基环戊烯的结构应修改为 8β-羟基环戊烯。
• Total Synthesis of Cycloaraneosene, a Fundamental Hydrocarbon of “epi”-Fusicoccane Diterpenoids, and the Structure Revision of Its Congener, Hydroxycycloaraneosene
  作者：Nobuo Kato、Shinya Tanaka、Hitoshi Takeshita

  DOI：10.1246/cl.1986.1989

  日期：1986.11.5

  The 5-8-5-membered tricyclic diterpene, cycloaraneosene, has been totally synthesized via the stereoselective condensation of two units of optically active iridoids, Cope rearrangement and chemical reduction of the tetrasubstituted C=C bond. The NMR spectrum of synthetic 9α-hydroxycycloaraneosene was not identical with the congener product, and the natural alcohol is likely to be 8β-hydroxyl derivative.

  通过立体选择性缩合两个单元的光学活性虹彩、科普重排和四取代 C=C 键的化学还原，完全合成了 5-8-5 元三环二萜环胂烯。合成的 9α-hydroxycycloaraneosene 的核磁共振谱与同系物不完全相同，天然醇可能是 8β-hydroxyl 衍生物。