(3S)-1-iriden-7-ol | 105576-35-0

• 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: (3S)-1-iriden-7-ol
• 英文别名: (+)-3(S)-isopropyl-1-methyl-2-(hydroxymethyl)cyclopent-1-ene；[(5S)-2-methyl-5-propan-2-ylcyclopenten-1-yl]methanol
• CAS: 105576-35-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: GUBQTGARQVDTNN-VIFPVBQESA-N

物化性质

• 沸点：
  216.4±8.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S)-1-iriden-7-ol 以80%的产率得到
  参考文献：
  名称：

  MEHTA, GOVERDHAN;KRISHNAMURTHY, NACHARAJU, TETRAHEDRON LETT., 28,(1987) N 47, 5945-5948

  摘要：

  DOI：
• 作为产物：
  描述：

  甜橙提取物 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (3S)-1-iriden-7-ol
  参考文献：
  名称：

  An enantioselective approach to dolastane diterpenes. Total synthesis of marine natural products (+)-isoamijiol and (+)-dolasta-1(15),7,9-trien-14-OL

  摘要：

  DOI：

  10.1016/s0040-4039(01)81097-2

文献信息

• Chiral Synthons from Monoterpenes.¹Stereoselective Syntheses of (-)5S, 6S, 9R-6-Isopropyl-9-Methyl-2-Oxaspiro[4.4]Nonan-3-One and (-) 3aR, 6R, 7aR-3a-Methyl-6-Isopropenylhexahydrobenzofuran-2-One
  作者：A. Srikrishna、G. V.R. Sharma、S. Nagaraju

  DOI：10.1080/00397919208019303

  日期：1992.5

  Highly stereoselective syntheses of two C-12 chiral synthons 3 and 9, mentioned in the title, starting from the monoterpenes R-1 imonene and R-carvone, using radical cyc 1 sation as key reaction, are described.

  描述了标题中提到的两个 C-12 手性合成子 3 和 9 的高度立体选择性合成，从单萜 R-1 imonene 和 R-carvone 开始，使用自由基环 1 基化作为关键反应。
• Application of microwave heating technique for rapid synthesis of γ,δ-unsaturated esters
  作者：Adusumilli Srikrishna、Sankuratri Nagaraju、Paturu Kondaiah

  DOI：10.1016/0040-4020(94)01058-8

  日期：1995.2

  The use of microwave heating technique for the acceleration of ortho ester Claisen rearrangement (a three step transformation) is described. Irradiation of a DMF solution of the allyl alcohol , triethyl orthoacetate and propionic acid (catalytic) in an Erlenmeyer flask for 10 minutes in a microwave oven generated the ester in 83% yield. Analogously, ortho ester Claisen rearrangement of a variety of

  描述了使用微波加热技术加速原酸酯克莱森重排（三步转化）。将烯丙醇，原乙酸三乙酯和丙酸的DMF溶液在微波炉中在锥形烧瓶中辐射10分钟（生成酯），产率为83％。类似地，原酸酯克莱森多种烯丙基和炔丙基醇的重排（，）得以实现。在15分钟内通过两个烯丙醇部分的原酸酯Claisen重排（涉及六个步骤）由2-丁炔-1,4-二醇（）形成二酯，证明了微波加热技术的多功能性。
• 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。
• Terpenoids to terpenoids: enantioselective construction of 5,6-, 5,7-, and 5,8-fused bicyclic systems. Application to the total synthesis of isodaucane sesquiterpenes and dolastane diterpenes
  作者：Goverdhan Mehta、Nacharaju Krishnamurthy、Srinivas Rao Karra

  DOI：10.1021/ja00015a034

  日期：1991.7

  The prevalence of a C12 common core (10) in C15-C30 terpenoids has been recognized. Construction of two ''chirons'' ((-)-11 and (-)-12a,b), corresponding to 10, from abundantly available (R)-(+)-limonene has been achieved through diastereoselective [3s.3s] sigmatropic processes 16 --> 11 and 19 --> 12, respectively. Chirons 11 and 12 have been successfully annulated to bicyclic hydrindanones 21, 23, and 30, hydrazulenoids 31-33, and 5,8-fused system 42 through methodologies that are short and practical. Thus, these enantiomerically pure bicyclics are available as advanced building blocks for higher terpene synthesis. One of the hydrazulenoids ((-)-31) has been elaborated to isodaucane sesquiterpenes (+)-aphanamol I (2) and (+)-2-oxoisodauc-5-en-12-al (46) through a novel restructuring protocol (31 --> 50). The stereo- and enantioselective synthesis reported here has established the absolute stereochemistry of isodaucane sesquiterpenes. The hydrazulenoid (-)-31 has also been deployed for the first enantioselective synthesis of oxygenated dolastane diterpenes (+)-isoamijiol (63) and (+)-dolasta-1(15),7,9-trien-14-ol (64). The key step in this venture was the stereoselective annulation of a six-membered ring through radical-induced alkyne-carbonyl cyclization (67 --> 68).