5',5',8'a-trimethyl-3',5',8',8'a-tetrahydro-spiro<1,3-dioxolane-2,1'(2'H)naphthalene>-6'(7'H)-one | 131613-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5',5',8'a-trimethyl-3',5',8',8'a-tetrahydro-spiro<1,3-dioxolane-2,1'(2'H)naphthalene>-6'(7'H)-one
• 英文别名: 1,1-ethylenedioxy-5,5,8a-trimethyl-1,2,3,4,6,7,8,8a-octahydro-6-oxonaphthalene；5',5',8'A-trimethyl-3',7',8',8'a-tetrahydro-2'H,5'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'-one；5',5',8'A-trimethyl-3',7',8',8'a-tetrahydro-2'H,5'H-spiro[[1,3]dioxolan-2,1'-naphthalin]-6'-on；1',1',4'a-Trimethylspiro[1,3-dioxolane-2,5'-3,4,6,7-tetrahydronaphthalene]-2'-one
• CAS: 131613-90-6
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: BFOBPDHTUCLGAA-UHFFFAOYSA-N

物化性质

• 沸点：
  150 °C(Press: 2 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5',5',8'a-trimethyl-3',5',8',8'a-tetrahydro-spiro<1,3-dioxolane-2,1'(2'H)naphthalene>-6'(7'H)-one 在 palladium on activated charcoal sodium tetrahydroborate 、 正丁基锂 、 氢气 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (+-)-5,5,8a-trimethyl-(4ar,8at)-octahydro-naphthalen-1-one
  参考文献：
  名称：

  烷基烯醇醚的二氯卡宾加合物作为呋喃的前体：在呋喃倍半萜烯（±）-pallescensin A的全合成中的应用

  摘要：

  从已知的反式-十氢萘酸酯2合成标题天然产物1时，已经采用了一种将呋喃环化成酮的新方法，其中涉及用碱处理衍生的甲基烯醇醚的二氯卡宾加合物。

  DOI：

  10.1016/j.tetlet.2006.07.068
• 作为产物：
  描述：

  3',4',8',8'a-tetrahydro-8'a-methylspiro[1,3-dioxolane-2,1'(2'H)-naphthalen]-6'(7'H)-one 、 碘甲烷 在 potassium tert-butylate 作用下， 以91%的产率得到5',5',8'a-trimethyl-3',5',8',8'a-tetrahydro-spiro<1,3-dioxolane-2,1'(2'H)naphthalene>-6'(7'H)-one
  参考文献：
  名称：

  Stereoselective Synthesis of (±)-7β-Acetoxyvouacapane

  摘要：

  通过 2-甲基-3-糠酸的烷基化反应和对甲苯磺酰腙的立体选择性还原水解，立体选择性地合成了四环呋喃二萜--7β-乙酰氧基瓦卡潘烷。

  DOI：

  10.1246/cl.1993.2117

文献信息

• Zur Kenntnis der Triterpene. 193. Mitteilung. Synthese von (�)-trans-4,4,7,9-Tetramethyl-3?-hydroxy-decalon-(8)
  作者：J. Kalvoda、H. Loeffel

  DOI：10.1002/hlca.19570400731

  日期：——

  Racemic trans-4,4,7,9-tetramethyl-3 β-hydroxy-decalone-(8) (Xa) has been synthesized. The corresponding optically active levorotatory compound had been previously obtained by R. Rüegg, J. Dreiding, O. Jeger and L. Ruzicka, as a degradation product of α-amyrin. The stereoisomer racemic cis-4,4,7,9-tetramethyl-3 α-hydroxy-decalone-(8) (XIVa) and the two hydroxyketones (±)-trans-4,4,7-trimethyl-3 β-hydroxy-decalone-(8)

  已经合成了外消旋的反式-4,4,7,9-四甲基-3β-羟基癸酮（8）（Xa）。相应的旋光性左旋化合物是先前由R.Rüegg，J.Dreiding，O.Jeger和L.Ruzicka作为α-amyrin的降解产物而获得的。立体异构体外消旋体顺式4,4,7,9-四甲基-3α-羟基十酮-（8）（XIVa）和两个羟基酮（±）-反式-4,4,7-三甲基-3β-羟基-十酮还获得了-（8）（XIIIa）和（±）-顺-4,4,7-三甲基-3β-羟基-癸酮-（8）（IXa）作为合成的副产物。
• A Synthesis of Taxanes by Lactam-sulfoxide Ring Contraction and Intramolecular Pinacol Coupling
  作者：Kazuhiko Takatori、Yoshinari Takeuchi、Yuka Shinohara、Kenji Yamaguchi、Masayuki Nakamura、Tatsuya Hirosawa、Takeshi Shimizu、Masae Saito、Shouich Aizawa、Osamu Sugiyama、Yasuo Ohtsuka、Masahiro Kajiwara

  DOI：10.1055/s-1999-3101

  日期：——

  A synthesis of the taxane ring system is described. The A-ring moiety 5, containing the carbons for construction of the B-ring, was prepared from Wieland-Miescher ketone via Beckmann fragmentation of the oxime 10. The B-ring was formed by means of 12-membered lactam-sulfoxide ring contraction. The formation of the C-ring was carried out by aldol condensation of the resulting AB-ring moiety 3 followed by intramolecular pinacol coupling to give the tricyclic diol 23.

  本文介绍了一种紫杉烷环系统的合成方法。A 环分子 5 含有用于构建 B 环的碳原子，由 Wieland-Miescher 酮通过肟 10 的贝克曼破碎法制备而成。B 环是通过 12 元内酰胺-亚砜环收缩形成的。C 环的形成是通过 AB 环分子 3 的醛醇缩合，然后通过分子内频哪醇偶联得到三环二醇 23。
• Stereoselective Synthesis of (±)-7β-Acetoxyvouacapane
  作者：Feng Wang、Kazuhiro Chiba、Masahiro Tada

  DOI：10.1246/cl.1993.2117

  日期：1993.12

  A tetracyclic furano diterpene, 7β-acetoxyvouacapane was stereoselectively synthesized via the route involving alkylation reaction of 2-methyl-3-furoic acid and stereoselective reductive hydrolysis of a tosylhydrazone.

  通过 2-甲基-3-糠酸的烷基化反应和对甲苯磺酰腙的立体选择性还原水解，立体选择性地合成了四环呋喃二萜--7β-乙酰氧基瓦卡潘烷。
• Chemobiological transformations of octalone and hydrindenone derivatives
  作者：Siméon Arseniyadis、Ricardo Rodriguez、Manuel Muñoz Dorado、Rosemeire Brondi Alves、Jamal Ouazzani、Guy Ourisson

  DOI：10.1016/s0040-4020(01)85563-0

  日期：1994.1

  Examples are given for allylic hydroxylations with Rhizopus arrhizus ATCC 11145. Chemical allylic hydroxylations are compared with microbiological ones. Stereoselective lipase-catalyzed hydrolyses are used efficiently.
• Correction of the Structure of a New Sesquiterpene from <i>Cistus</i> <i>c</i><i>reticus</i> ssp. <i>c</i><i>reticus</i>
  作者：Konstantinos Hatzellis、Georgia Pagona、Apostolos Spyros、Costas Demetzos、Haralambos E. Katerinopoulos

  DOI：10.1021/np0498556

  日期：2004.12.1

  In an attempt to identify the structure of a sesquiterpene from Cistus creticus ssp. creticus proposed in the literature as 1,1,4a,6-tetramethyl-5-methylene-1,2,3,4,4alpha,5,8,8alpha-octahydronaphthalene, the synthesis of its cis isomer 2 was carried out in 11 steps and 9.5% yield. Comparison of the spectra of 2 and those reported earlier for the synthetic trans isomer 1 with the spectral profile of the isolated natural product indicated that the latter was not compatible with either 1 or 2. The correct structure was assigned, by detailed spectroscopic analysis of the natural product, as 6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (3).